Islamorada Vacation Rentals

(107 rentals)
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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$214

avg/night

$214
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This condo is located in one of Islamorada's most prestigious condo complexes. PROPERTY NAME: Beacon Reef #407 83201 Old Highway, Islamorada, Florida LOCATION: Ocean side Condo MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed MILE MARKER: 83.2 DETAILS: ...

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Property Type

Islamorada Condo

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
last minute deal
LAST MINUTE DEAL 12/12 - 1/23: Escape the cold! Islamorada ocean view condo with 30' boat slip for only $400/per night.

$428

avg/night

$428
avg per night
Offer for: Dec 12 - Jan 23:
Escape the cold! Islamorada ocean view condo with 30' boat slip for only $400/per night.

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Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Mother Ocean! This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room ...

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Property Type

Islamorada Condo

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DEAL
Islamorada House
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
3 reviews

Distance to beach: 2 miles to Founders Park

$699

avg/night

$699
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios ...

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Property Type

Islamorada House

Featured review

"You found it"

If you’re looking for a well kept beautiful home, right on the water positioned right between the Gulf and Atlantic, great pool and hot tub YOU FOUND IT. Communication is great and owner is so helpful. ...

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Islamorada House | On the beach
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$946

avg/night

$946
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Introducing the "Bonefish House" at Tarpon Point! This opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed ...

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Property Type

Islamorada House

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Islamorada Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
owner special
Owner special: Available weekly or monthly from January 1, 2025 due to cancellation

$496

avg/night

$496
avg per night
Owner special:
Available weekly or monthly from January 1, 2025 due to cancellation

View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This Condo comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks.

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Property Type

Islamorada Condo

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Islamorada House | On the beach
6 BR | 7.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 7.5 bathrooms

Distance to beach: 1 feet to on property or at Founders Park

$371

avg/night

$371
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Beautiful new home on Florida Bay with sandy beach, spacious pool, beautiful views, and sunsets every night. Three Private Suites are offered to accommodate up to 12 guests. Each suite can be rented individually or combined. I would be happy to discuss your needs and answer any questions you may have. ...

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Property Type

Islamorada House

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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 3 miles to Anne's Beach State Park

$314

avg/night

$314
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

This 3-bedroom bayfront property is located on Lower Matecumbe in Islamorada. The view is spectacular with sunsets on the water most of the year. There is plenty of room for boat trailers, RVs and other toys inside the fence. There is covered parking for your vehicles and a seawall out front to tie your ...

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Property Type

Islamorada House

Featured review

"Lower Matecumbe"

All I can say is that this place never fails to impress! The views from every inch of the property are the best in all of the keys! Great communication with Rich and his office. Would recommend every ...

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Islamorada House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
last minute deal
LAST MINUTE DEAL 1/3 - 1/4: January is available!! Call Rich for special pricing . Be the first guests in new house

$618

avg/night

$618
avg per night
Offer for: Jan 3 - Jan 4:
January is available!! Call Rich for special pricing . Be the first guests in new house

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Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to your private slice of paradise in the heart of the Indian Waterways! This newly constructed Coastal Contemporary Caribbean-style home, with 165 feet of waterfront, invites you to experience the ultimate blend of luxury and tranquility. Unwind in Style: From the moment you step into the ...

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Property Type

Islamorada House

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DEAL
Islamorada House
4 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 3 bathrooms
3 reviews

$525

avg/night

$525
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

PLEASE INQUIRE WITHIN FOR ALL STAYS AND SPECIAL DEALS!!! OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access. This Open Water home HAS IT ALL. -Brand New (Sept 2017) Huge, heated ...

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Property Type

Islamorada House

Featured review

"Love this house"

Great location! Sunrises and sunsets were amazing. Easy location to open water, kids loved going out on boat. Fishing right off the dock. Lots of wildlife. Everyone loved the outdoor bathroom! Very convenient. ...

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Islamorada Villa
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
14 reviews

Distance to beach: 5 miles to Anne's Beach

$325

avg/night

$325
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

The "Nest" villa (one of 7 privately owned condo residences) sits on a 1 acre lot located on Islamorda's beautiful Florida Bay. Stunning water views and unforgettable sunsets are guarenteed. The property is filled with mature tropical landscaping along a tree lined private gravel driveway ...

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Property Type

Islamorada Villa

Featured review

"Amazing location, view, and super clean!"

My 18 yr old son and I stayed here at the end of September and it was a fantastic trip! We have been going to the keys for 14 years several times a year. This unit is the cleanest we have ever seen! ...

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$195

avg/night

$195
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

3 Beds/2 bath townhouse in Islamorada, Florida Keys. Ground Floor features a full kitchen, full bath, living room with large tv, dining room with views of the tennis court, outdoor patio with BBQ and additional dining table. Second Floor features a large full bath, 1 king size bed, 1 queen size bed, 2 ...

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Property Type

Islamorada Condo

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Islamorada House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
6 reviews
last minute deal
LAST MINUTE DEAL 12/9 - 12/23: Holiday Special - Book before December 25th, 2024 and save an additional 10% off for Jan, Feb or Mar

Distance to beach: 2 miles to Founders Park

Offer for: Dec 9 - Dec 23:
Holiday Special - Book before December 25th, 2024 and save an additional 10% off for Jan, Feb or Mar

View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to your dream getaway in Islamorada! This 3-bedroom, 2.5-bath paradise boasts a gourmet kitchen with a Viking gas stove, a spacious dining area, and Internet-ready TVs for game days or movie nights. On the first floor, you will find two bedrooms, a full bathroom and a large entertainment area ...

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Property Type

Islamorada House

Featured review

"Awesome House & Canal"

We had a wonderful time here. The location is perfect. Close to restaurants, shops, and attractions. We spent a lot of time floating and frolicking in the canal. The house was spotless. The kitchen was ...

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DEAL
Islamorada House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
16 reviews

$367

avg/night

$367
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2022 Remolded bathrooms, 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 8. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house ...

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Property Type

Islamorada House

Featured review

"The BEST of the BEST in every way!"

By far and away, this was the best rental property we have ever stayed! We have been visiting Islamorada for nearly 20 years and have stayed almost everywhere you can imagine, and we have now struck gold ...

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Islamorada Townhome
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2.5 bathrooms

$284

avg/night

$284
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking ...

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Property Type

Islamorada Townhome

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Islamorada House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Distance to beach: 0.5 miles to White Marlin Beach

$702

avg/night

$702
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Bring your boat and Jet Skis Nestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. New heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, double jet ski lift, and two floors facing ...

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Property Type

Islamorada House

Featured review

"Fabulous location, off the beaten path, clean, owner available for questions and very responsive."

We stayed in this home for a month, the location is amazing if you love to paddle board, kayak and discover the many mangrove islands that are a five minute paddle from your dock. The outside area has ...

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Islamorada House | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
9 reviews
owner special
Owner special: Available starting January 6 Looks better in person than pictures!

Distance to beach: 0.5 miles to White Marlin Beach

$643

avg/night

$643
avg per night
Owner special:
Available starting January 6 Looks better in person than pictures!

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6 Pure High End Luxury with all the Bells and Whistles Boat Friendly Vacation Rental with Dock Villa Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. ...

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Property Type

Islamorada House

Featured review

"Perfect, quiet, and secluded"

This was a spectacular vacation! The house was clean and comfortable, and the location was quiet and the setting perfect. I could write a novel about the host and the house, but in a few words the host ...

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 1 miles to Anne's Beach State Park

$369

avg/night

$369
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This Condo sleeps 4 and comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key, Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks. Newly refurnished and refurbished, ...

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Property Type

Islamorada Condo

Featured review

"A great two weeks in beautiful Islamorada."

This two bedroom apartment in the beautiful Bay Harbour condominium was special. The views of the ocean and the apartment complexes marina were exceptional. The apartment was well stocked with all the cooking ...

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Islamorada House
2 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 2 bathrooms
7 reviews

$368

avg/night

$368
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

1440 sf - Sleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community ...

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Property Type

Islamorada House

Featured review

"BEST TROPICAL VACATION EVER!!!!!!!!"

Here is the review I am trying to post via for our March 2024 stay. Wonderful! Fantastic! Amazing! Wonderful Hosts!!! Jay and Sharon are so welcoming and supportive! We felt at home before we ...

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Islamorada House | On the beach
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$1375

avg/night

$1,375
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Immerse yourself in the luxury and beauty of Oceanside, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends. ...

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Property Type

Islamorada House

Featured review

"Beautiful stay"

We had the best time at this house! Giovanna and her husband were wonderful hosts and were on top of everything we needed. The house itself is in a great location close to shops and restaurants. Book the ...

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Islamorada Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

$123

avg/night

$123
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys. Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance. 2 ...

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Property Type

Islamorada Condo

Featured review

"Beautiful Oceanfront Condo"

Plantation by the Sea is an older condo complex that is beautifully maintained. The condo is located at MM 87.5 just off of U.S. 1 in the heart of Islamorada. Restaurants of various types can be found within ...

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Islamorada House | On the beach
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
7 reviews

$957

avg/night

$957
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

‘The Beach House’ at Tarpon Point in Islamorada- DIRECT RENTAL WITH NO ADMIN OR CC FEES Do not be deceived by other units' lower "nightly rates"; we are the largest/most private unit and have the lowest total rental cost! Why pay more for less? ‘The Beach House’ ...

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Property Type

Islamorada House

Featured review

"Very peaceful and beautiful accommodations"

Impressive location. View from master bedroom is fantastic. House was clean, comfortable, well furnished and great layout. Area is easy to navigate and lots of great restaurants close bye. Green Turtle ...

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Islamorada House
2 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 2 bathrooms
2 reviews

$120

avg/night

$120
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Located at Mile Maker 87 Bayside. This gated condo complex offers a large heated pool, club house, Jacuzzi, two tennis court, large Bayside beach. This townhouse (sleeps 8) has just been totally renovated with beautiful tropical furniture, all new kitchen, small garden patio with hammock, living room ...

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Property Type

Islamorada House

Featured review

"Great vacation"

We have never stayed in the Florida Keys before so this was a new adventure that we will definitely do again. The weather was a perfect 80 degrees. Nothing but chill time. We would start the day in the ...

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$210

avg/night

$210
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This condo is located in one of Islamorada's most prestigious condo complexes. PROPERTY NAME: Beacon Reef #414 83201 Old Highway, Islamorada, Florida LOCATION: Ocean side Condo MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed MILE MARKER: 83.2 DETAILS: ...

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Property Type

Islamorada Condo

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Islamorada Apartment | On the beach
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
46 reviews

$174

avg/night

$174
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach ...

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Property Type

Islamorada Apartment

Featured review

"Slice of Paradise"

We’ve been coming to the Keys for 20 years and this place takes the win. Jerry and Lisa are so friendly and make you feel very welcome and comfortable. The apartment has everything you need including ...

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Islamorada House | On the beach
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

$1346

avg/night

$1,346
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experience for those looking for a luxurious and private getaway. Each spacious bedroom and en suite bathroom is inspired by modern coastal furnishings. Perfect for entertaining family and friends, ...

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Property Type

Islamorada House

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Islamorada House | On the beach
3 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3.5 bathrooms
24 reviews

$1363

avg/night

$1,363
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe, so you are a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned for the discerning traveler. You will escape ...

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Property Type

Islamorada House

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Islamorada House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms
15 reviews

$833

avg/night

$833
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

There's a reason why we have ALL 5-star reviews! HeartofMorada is located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries that you will love! The home is just 3 years old and WELL apportioned with everything you'd need on vacation and ...

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Property Type

Islamorada House

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Islamorada House | On the beach
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Distance to beach: 50 yards to Private sunning beaches at Anglers

$658

avg/night

$658
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

SAVE VRBO's $500-600 Booking fee!! Welcome to Anglers Reef, a very special community of vacation homes. And to Anglers Reef 140's OceanFRONT location with its unique UNOBSTRUCTED OCEAN VIEWS FROM EVERY ROOM and spacious wraparound decks! Boat slip is optionally available for $375/wk, Christmas ...

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Property Type

Islamorada House

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Islamorada House
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 0.3 miles to Anne's Beach

$145

avg/night

$145
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Enjoy this modern lagoon front ground-level one-bedroom apartment in a single-family home with exclusive use of backyard, pool, dock, and carport. Located on the Gulf side of Lower Matecumbe (Islamorada MM 73.5), minutes from the Channel 2 and Channel 5 Bridges, offering immediate access to the Oceanside. ...

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Property Type

Islamorada House

Featured review

"Overall excellent .... very comfortable for two with great outdoor ammenities."

this property was great for us as an older couple....park under cover steps from the front door..beautiful pool and canal front and a quiet location. the home is clean and easy to care for and the owner ...

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews
owner special
Owner special: Available from January 4. weekly or Monthly

$362

avg/night

$362
avg per night
Owner special:
Available from January 4. weekly or Monthly

View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This Condo is located on Lower Matecumbe Key, close to restaurants, shopping and Tiki bars. With pool, tennis courts and a protected marina, Bay Harbour is a preferred residence for repeat visitors to the Keys. Elevators for easy access and a second floor location make it easy to enjoy your stunning view ...

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Property Type

Islamorada Condo

Featured review

"Feels like home"

We have rented a condo at Bay Harbour for many years now. We love the location and the complex amenities. I fish a lot so my husband is happy with the workout room, pool, safe bike paths, hot tub and ...

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Islamorada House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Rentals by owner
  • WiFi

About this property

Beautiful, fully remodeled waterfront home with water on both sides! Ocean and lagoon views from bedrooms, dining room, balconies and kitchen. Cable TV with premium channels and wi-fi internet access. The home is in a quiet neighborhood on a cul-de- sac and very convenient to Tavernier or Islamorada ...

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Property Type

Islamorada House

Featured review

"A rental that exceeded expectation"

A well maintained home in a perfect quiet setting. The owner Patrick was outstanding to work with and made sure that all was in order. He is an excellent communicator. Welcome bottles of wine greeted us. ...

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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs ...

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Property Type

Islamorada Condo

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Islamorada Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms

$545

avg/night

$545
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful views from this condo! Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL. We are new owners of this condo that has never been in the rental pool. (that is why few reviews) Complete remodel with no expense spared! The location is quiet with the most beautiful ...

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Property Type

Islamorada Condo

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Islamorada House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms

$1935

avg/night

$1,935
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This grand peninsula retreat is embraced by the Ocean and lush mangroves, offering privacy to the heated pool with its tiki bar, expansive sandy playgrounds and lounge areas. Nestled along the tranquil shores of Florida Bay, its array of indoor and outdoor living areas, dock with ocean-access canal, gazebo ...

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Property Type

Islamorada House

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Islamorada House | On the beach
5 BR | 5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 5 bathrooms

$820

avg/night

$820
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

One of the only white sandy beaches in the Fl Keys and 1 mile whole of it! Newly built,state of the art,beautifully done 5 bedroom home, 4 master suites w/ king beds and facing open water! Magnificent indoors and out! Each bathroom is exquisite,very large stone,glass and hand picked tiles. The ...

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Property Type

Islamorada House

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Islamorada House
4 BR | 2 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 2 bathrooms
4 reviews

$257

avg/night

$257
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

ALERT: BRAND NEW POOL JUST COMPLETED AND INSTALLED.... DOWNSTAIRS IS AVAILABLE TO RENT BUT IS NOT INCLUDED IN THE PRICE feel free to ask about downstairs pricing and availability. Downstairs is an additional 3br and 2ba so the upstairs and downstairs would be a total of 7br & 4ba.... THIS LISTING ...

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Property Type

Islamorada House

Featured review

"A month in heaven"

My wife and I spent the month of Dec. 2022 at this property in Islamorada (HEAVEN) in the Keys. The property has a pool, a canal and a boat dock that can handle any boat. Let me start of saying that ...

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Islamorada Condo
1 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 2 bathrooms

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

A beautiful piece of serenity and paradise can be yours, available for seasonal rental from January through April. Islamorada the fishing dream of all sport and causal fishing enthusiast. But if you don't fish (that is a shame) you can enjoy the wonderful dining, the historic parks, diving and ...

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Property Type

Islamorada Condo

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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 100 feet to Front door

$231

avg/night

$231
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

MINIMUM STAY: 30 days Spacious and beautiful 2 bedroom/2 bath ocean front condo unit with unobstructed ocean views. BOAT SLIP is available upon request for up to a 46 foot boat, low tide draw is 30 inches. There is an additional fee for boat slip. Walk out your front door and go boating. You’ll ...

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Property Type

Islamorada Condo

Featured review

"Ocean Harbor M3 is Fabulous!"

Priceless view of the ocean. Nice marina. Workout room is great with a view. The condo is clean and spacious. Every thing you need is here. Very easy to maintain. During my 3 month stay from May to August ...

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$257

avg/night

$257
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Tropically furnished condominium with amazing views of the Gulf of Mexico, located at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. It is centrally located, with easy access to Restaurants, shopping ...

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Property Type

Islamorada Condo

Featured review

"Fantatic"

Fantastic host. fantastic location, fatastic accomodations! Looking forward to returning in 2022. Thank you Susan

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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review
owner special
Owner special: 15% off Jan1 through Feb 4 2024. I rent from Saturday to Saturday so take 1 2 3 or 4 weeks Remodeled

$322

avg/night

$322
avg per night
Owner special:
15% off Jan1 through Feb 4 2024. I rent from Saturday to Saturday so take 1 2 3 or 4 weeks Remodeled

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

We have owned and rented this property for 20 years and have been coming to Seagulls Condominiums for over 40 years. The condo bathrooms and bedrooms have just been updated and the entire building has just finished a major upgrading and painting. If my pics don't import from vrbo 49422, then you ...

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Property Type

Islamorada Condo

Featured review

"Outstanding view and amenities. Will return soon!"

Classic art deco style building which was fully remodeled both inside and out. The owners are very responsible and have been doing this a long time.

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Islamorada House | On the beach
6 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5 bathrooms

$5486

avg/night

$5,486
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to Caribee Beach House! Discover the enchanting charm of Caribee Beach House, where the timeless allure of old-school Islamorada beautifully melds with stylish comforts. Tucked away in the heart of downtown Islamorada, this hidden gem offers an extraordinary retreat with 200 feet of private ...

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Property Type

Islamorada House

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Islamorada Townhome
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms
3 reviews

Distance to beach: 0.5 miles to Port Antigua Private Beach

$440

avg/night

$440
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

This recently renovated property enjoys 6 bedrooms, 4 bathrooms and separate kitchens, living rooms and laundry facilities. It shares an ocean facing veranda with 2 dual gas grills and multiple seating and lounging areas. It has ample offstreet parking for vehicles and trailers. The Admiral on the Cove ...

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Property Type

Islamorada Townhome

Featured review

"A Spectacular Spot"

We enjoyed our stay at this beautifully furnished and well stocked house. George and Bonnie responded quickly to any questions that we had. The separate living areas allowed us to enjoy family and friends ...

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Islamorada House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms

$556

avg/night

$556
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Paradise Palms! Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-bath home serves as an excellent setting for your tropical getaway. Ideally located in Islamorada on Lower Matecumbe Key, you will have convenient access ...

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Property Type

Islamorada House

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Islamorada Apartment
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
5 reviews

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

The apartment is in a house on the canal and across from the beach with beach access. It is situated on the ground floor of a two storey Keys house where you would be the only residents. All the amenities would be yours and you would have space, tranquility and privacy in the tropically planted landscape. ...

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Property Type

Islamorada Apartment

Featured review

"Perfect rental for one couple"

This is the perfect apartment for one couple. Wonderful location on the oceanside with ocean views across the street. Has a great dock for your boat with great ocean access. Fish cleaning table is under ...

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Islamorada House | On the beach
9 BR | 8 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 8 bathrooms

$1781

avg/night

$1,781
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to Infinity Bay Islamorada, an infinite paradise with infinite possibilities in the heart of the Florida Keys. This exclusive property offers a blend of sophistication and tranquility, where guests can unwind in style against the backdrop of crystal-clear turquoise waters and swaying palm trees. ...

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Property Type

Islamorada House

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Islamorada Apartment
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms

$133

avg/night

$133
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Gorgeous 2 bedroom 1 & half condo, two story (townhouse style) HEATED POOL, DOCK FOR FISHING, OCEAN FRONT location. Gated community makes it a perfect getaway for a family for 4 but sleeps 6 to accommodate any short term visitors. Inside our home, you will find all the amenities for an enjoyable stay, ...

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Property Type

Islamorada Apartment

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Islamorada Villa
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$450

avg/night

$450
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to “At The Sandbar!” This newly built oceanside villa in Islamorada is a wonderful choice for those seeking a serene retreat and an opportunity to immerse themselves in the relaxed nature of the Florida Keys. Situated within the Peaceful Palms community on Windley Key, this three-bedroom, ...

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Property Type

Islamorada Villa

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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 100 yards to Port Antigua Private Beach

$358

avg/night

$358
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

February 1-28 still available This spectacular 3/Bed 2/Bath canal front home is located in Lower Matecumbe Key, a part of Islamorada island. Enjoy the exclusive neighborhood of Port Antigua—just a 5 minute walk to our private beach. The house is nautically designed, with a spacious and open ...

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Property Type

Islamorada House

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
12 reviews

Distance to beach: 4 miles to Anne's Beach

$332

avg/night

$332
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy the sunrise from the balcony or from in the condo through 50 ft of glass sliding doors. You can also see the sunset from our walkway on bayside. We have a full kitchen from dishwasher to microwave, washer/dryer, even beach towels. We have wifi, cable TV, and a Master Bath with whirlpool tub, ...

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Property Type

Islamorada Condo

Featured review

"EXCELLENT CONDO"

We had a fabulous time at this condo. Spectacular views, great fishing. Close to EVERYTHING. The condo was spacious and VERY CLEAN. EVERYTHING you would need for a fun time was here.. will be back again ...

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Islamorada Cottage
2 BR | 1 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1 bathroom

$143

avg/night

$143
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to the "Keys Life Cottage!" This beautifully updated and spacious two bedroom, one bath home is tucked away on a large landscaped lot in the heart of Islamorada and within walking or biking distance to Islamorada's famed Arts and Cultural district and to some of the most renowned ...

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Property Type

Islamorada Cottage

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Islamorada Vacation Rentals

Islamorada Weather

 | 

7524°  6217°
JANUARY
Ocean 7423°
7624°  6217°
FEBRUARY
Ocean 7423°
7826°  6518°
MARCH
Ocean 7624°
8228°  7021°
APRIL
Ocean 7926°
8529°  7423°
MAY
Ocean 8127°
8731°  7725°
JUNE
Ocean 8329°
8932°  7926°
JULY
Ocean 8530°
8932°  7826°
AUGUST
Ocean 8730°
8731°  7725°
SEPTEMBER
Ocean 8530°
8429°  7423°
OCTOBER
Ocean 8328°
8027°  7021°
NOVEMBER
Ocean 7926°
7624°  6518°
DECEMBER
Ocean 7625°

Find Your Ultimate Vacation with Islamorada Vacation Rentals


Islamorada is a small village located south of mainland Florida along the state’s gorgeous tropical keys. In fact, Islamorada vacation rentals and the village in which they reside encapsulate six of the Florida Keys and is known as one of the most beautiful vacation destinations throughout Florida. 

Plus, Islamorada is often called the “Sport Fishing Capital of the World,” making it a great place to visit for those who enjoy fishing for sport or recreation. 

Due to its separation from mainland Florida, Islamorada is made up mostly of white-sand beaches and clear waters, which offer plenty of opportunity for some peaceful R & R as well as all of the oceanside water sports you could imagine. 

Swim with the dolphins, take a snorkeling excursion, ride the waves on your surfboard, or simply relax on the beach with a good book; whatever you choose to do, you’re sure to have an incredible experience in Islamorada. 

In a village as unique and special as Islamorada, the best way to get the most out of your vacation is to browse Islamorada vacation rentals instead of opting for a hotel.

Hotels are crowded and impersonal, but your Islamorada home rental will be a one-of-a-kind space completely dedicated to you and your family. Plus, you’ll be able to live the life of a local and enjoy the unique architecture of the Florida Keys from a new perspective in your Islamorada rental home.

How to Get the Most out of Your Islamorada Vacation


As a tropical location, Islamorada sees steady rainfall throughout the year as well as relatively high levels of humidity, especially in the summer months. The rainiest seasons tend to be early summer and early autumn, making springtime and late autumn the best times of year to visit Islamorada in order to enjoy the best possible weather. 

Since the Florida Keys are separated from mainland Florida by several miles of ocean, most tourists will access the islands by air instead of by car, even if they’re already Florida residents. 

The Florida Keys/Marathon International Airport is the easiest way to access the city, and vacationers can reach Islamorada from the airport within a 40-minute drive by way of the Overseas Highway.

Best Activities Nearby Islamorada House Rentals


You can’t get much closer to ocean wildlife than on the Florida Keys, which is why Islamorada’s Wild Dolphin Tours are so wildly popular. 
Get to know the resident dolphins of the Florida coast by swimming alongside them and experience many other incredible types of aquatic creatures from a close range, all guided by locals who know the waters of the Florida Keys inside and out. 

With Wild Dolphin Tours in Islamorada, you can also opt to take a snorkeling excursion along the scenic coral reefs surrounding the islands with the Snorkel & Sandbar Boat Tours. 

These excursions include Alligator Reef, Florida Bay, and Cheeca Rocks, some of Florida's most stunning and highly sought-after coral reefs. Book a three-hour, four-hour, or private tour to create a one-of-a-kind experience for you and your family. 

There’s plenty more natural beauty to see in Islamorada apart from the expansive ocean views. Nature lovers will enjoy a trip to the Lignumvitae Key Botanical State Park, a unique botanical experience that features a variety of local plant life and even some opportunities to view Florida Keys wildlife. 
The park is open from 8 a.m. to 4 p.m. Thursday through Monday, and the entrance fee is $2.50 per person, with self-guided tour brochures available to get the most out of your visit. 

Looking to take in a bit of local history as you enjoy the gorgeous scenery? Pay a visit to Indian Key Historic State Park, the site of the original Dade County seat in 1836. 
In 1840, a group of local natives led by leader Chakaika raided the settlement and burned the town to the ground, leaving only one building behind. You can visit the remaining town building and learn more about the area’s unique history any day of the week between 8 a.m. and sunset, and the entrance fee is $2.50 per visitor.

Islamorada, FL, Annual Events


Island Fest is one of the most anticipated annual events in Islamorada. Taking place early each April, Island Fest features an art show and competition, unique food vendors, live music, a classic car show, and more. Plus, local food vendors go head-to-head to earn the sought-after People’s Choice Award for the best food of the festival. 
Another popular Islamorada event more heavily focused on the local art scene is the Morada Way Art Walk, a monthly event that showcases local art in a variety of mediums, including photography, painting, ceramics, and printmaking. The Morada Way Art Walk also features live musical acts and delicious dining options and is free to enter.

Best Food and Drink near Islamorada Rentals


If you’re looking to enjoy a fine meal with an unforgettable view of the ocean, there are many incredible options to suit your needs in Islamorada. Locals and visitors alike love Lorelei Restaurant & Cabana Bar, a fun semi-casual joint that serves a variety of fresh seafood entrees and boasts a full bar with unique cocktails to try. 

Islamorada also features the Islamorada Brewery & Distillery, the only establishment of its kind on the Florida Keys. Experience all that Islamorada has to offer with an incredible locally brewed beer in the beer garden, a refreshing hand-crafted cocktail, and delicious eats from local food trucks.


FAQ

How many vacation rentals are there in/around Islamorada?

There are 107 Islamorada vacation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Islamorada?

There are vacation rentals available in Islamorada for as low as $87 per night with an average price per night of $369.

Can I rent a house in Islamorada?

Yes, you can find house rentals in Islamorada close to Theater of the Sea, Florida Keys Brewing Company, and History of Diving Musem. Don't forget to stop in to Founder's Park or Alligator Reef.

Do any vacation rentals in Islamorada have a pool?

Yes there are 50 vacation rentals with a pool in Islamorada on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Islamorada vacation rentals on the ocean?

There are 51 oceanfront rentals in Islamorada available on FloridaRentals.com. Use our filters to search and book yours today!