Islamorada Rentals by Owner

(66 rentals)
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

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

"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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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Paradise Beautiful and breathtaking ocean views in Lower Matecumbe Key in Islamorada. Private Beach Access to the beautiful White Marlin Beach2/1 Master Bedroom - King size bed Second bedroom - full size bedInflatable full size bed available One full bath with bath tub Living room with ...

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Property Type

Islamorada Apartment

"Wow! What a fantastic place."

Well we definitely will return. Completely MORE than we expected. Very nice and the perfect amount of room for a small family or couples. Great hosts and very responsive. We could not have been any luckier.

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Rentals by owner

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

"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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

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

"4 years"

This was our 4th year on Tollgate and somehow it gets better. Tiff and Bill go above and beyond in accommodating us. The updates look fabulous, love the painting in the dining room. Our dog Max has made ...

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2 BR | 2 BA | Sleeps 4 | Quick View

1

$189

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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. Enjoy your morning coffee, watching the boats go out. Relax, ...

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Property Type

Islamorada Condo

"Fantatic"

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

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2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 100 feet to Front door

$153

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

MINIMUM STAY: 30 daysSpacious 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

"Nice condo with an amazing location"

Had a great stay at Ocean Harbor. Condo is nicely outfitted with everything we needed for our stay. Great location near many of the fishing and restaurants we like to visit. Would highly recommend!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • 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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5 BR | 3.5 BA | Sleeps 17 | Quick View

2

$2571

avg/night

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Key Amenities

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

About this property

Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and shopping. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat ...

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Property Type

Islamorada Estate

"Milestones Birthday Celebration /Family Vacation"

Absolutely beautiful home..Featured everything we needed to enjoy our vacation..Spacious enough for 14 people. Close to places if we decided to go out n explore..Epic week.!!Thank you

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2 BR | 2 BA | Sleeps 4 | Quick View

6

Distance to beach: 0.9 miles to Founders Park

$113

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Oceanfront gated community. Offers pool overlooking the ocean, pier which you can fish off of, clubhouse, sauna, exercise room, and very clean bathrooms by the pool. 2 Bed, 2 Bath. Master bedroom offers queen bed, sitting room, coffee, 50 inch smart tv, storage, master bath separate toilet. 2nd Bedroom ...

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Property Type

Islamorada Condo

"Perfect!"

Sharon’s condo was absolutely gorgeous! It was super clean upon arrival and had everything we could have needed for our 3 month stay (linens, dishes, pots & pans, cleaning supplies, etc). The interior ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Anglers Reef Villa Resort 2 Bedroom and 2.5 Bath Villa, in Anglers Reef with Boat Slip. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch ...

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Property Type

Islamorada House

"Awesome home"

Amazing home and location. Great customer support. Would love to return to here again. Islamorada is so beautiful

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

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

"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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4 BR | 4 BA | Sleeps 10 | Quick View

3

Distance to beach: 2 miles to Founders Park

$449

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

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

"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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3 BR | 2.5 BA | Sleeps 8 | Quick View

owner special
Owner special: August Rates Reduced $400-$600 per week! True Oceanfront - best location in Anglers Reef!

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

$497

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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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6 BR | 7.5 BA | Sleeps 12 | Quick View

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

$253

avg/night

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Key Amenities

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

About this property

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

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Property Type

Islamorada House

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$500

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Newly renovated 3/2 Canal front home with brand new pool, deck and front gates for privacy!The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms, ...

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Property Type

Islamorada House

"We love this house!"

2022 was our 2nd time renting this wonderful home. The location is fantastic, and the house and property offer everything you can imagine. Outside is a paradise with a refreshing pool (with fun lights ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

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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3 BR | 2.5 BA | Sleeps 6 | Quick View

6

Distance to beach: 2 miles to Founders Park

$475

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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

"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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4 BR | 4.5 BA | Sleeps 8 | Quick View

1

Distance to beach: 0.5 miles to White Marlin Beach

$736

avg/night

View Details

Key Amenities

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

About this property

Bring your boat and Jet SkisNestled 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

"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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3 BR | 2.5 BA | Sleeps 6 | Quick View

$559

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

This home has a private beach entrance directly into the bay and is across from Sea Oats Beach. Enjoy a quick paddle board or kayak trip directly out of the back door. Dock and boat lift avialble for 30+ foot boat. Unmatched views of both the Atlantic Ocean, Gulf ocean or both from every window and ...

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Property Type

Islamorada House

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3 BR | 2 BA | Sleeps 6 | Quick View

9

Distance to beach: 0.5 miles to White Marlin Beach

$643

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Rentals by owner

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 DockVilla 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

"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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5 BR | 5 BA | Sleeps 10 | Quick View

$627

avg/night

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Key Amenities

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

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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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

"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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

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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2 BR | 2 BA | Sleeps 4 | Quick View

owner special
Owner special: 15% off July

$200

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

I 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

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3 BR | 2 BA | Sleeps 6 | Quick View

11

Distance to beach: 4 miles to Anne's Beach

$265

avg/night

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Key Amenities

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

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

"Spacious, awesome condo with amazing views."

The condo was very spacious, meticulously clean and well supplied with cooking utensils and supplies. This was probably one of the nicest places we have stayed in the many years we have been going to the ...

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2 BR | 2.5 BA | Sleeps 6 | Quick View

2

$300

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

2 Bed & 2.5 Bath Villa in Anglers Reef with Boat slip.Upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, upstairs balcony. Spacious ...

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Property Type

Islamorada Villa

"Great accomodations"

Beautifully decorated house in the Keys. Very spacious and comfortable. Kitchen was fully stocked. Plenty of linens and extra towels. The community dock has kayaks we used. There are lobsters under ...

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3 BR | 2.5 BA | Sleeps 8 | Quick View

1

$650

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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

"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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4 BR | 4.5 BA | Sleeps 8 | Quick View

7
last minute deal
LAST MINUTE DEAL 7/27 - 8/17: Due to Cancellation 7/27-8/17 now 30% off! $4000/wk plus tax/fees~ Weekly Minimum~ 8 Max Occupancy

$571

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

‘The Beach House’ at Tarpon Point in Islamorada- DIRECT RENTAL WITH NO ADDITIONAL FEES‘The Beach House’ is a luxurious oceanfront home in a private gated enclave of only 12 houses. This end home offers privacy and beautiful ocean views including of Indian Key Historic State ...

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Property Type

Islamorada House

"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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DEAL

2 BR | 2 BA | Sleeps 4 | Quick View

13

Distance to beach: 5 miles to Anne's Beach

$301

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Rentals by owner

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

"Beautiful place!!"

Couldn't have been any better. Perfect location, comfortable beds, great views! The deck right out the door was our favorite place to be. Highly recommend the Nest

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6 BR | 4 BA | Sleeps 12 | Quick View

3

Distance to beach: 0.5 miles to Port Antigua Private Beach

$411

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Rentals by owner

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

"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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1 BR | 1 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.3 miles to Anne's Beach

$146

avg/night

View Details

Key Amenities

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

About this property

Enjoy this modern lagoon front ground level one bedroom condo/apartment with exclusive use of the 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 Ocean side. Dockage available ...

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Property Type

Islamorada Condo

"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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Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner

About this property

This condo is located in a tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yacht Club. FYC is a private 70-unit, gated community with a 53-slip marina and accommodations available for that tranquil tropical getaway you've always imagined. This condo offers ...

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Property Type

Islamorada Condo

"Location"

We have been searching for a unit in this area and found this. Islamorada has many restaurants, from fast food to white tablecloths, from waterfront dining to sports bars.

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Key Amenities

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

About this property

Magnificent brand new home nestled between Cheeca Lodge Resort and Caribbean Resort with its own private beach offering a unique and luxurious experience for those looking for a private getaway. This 4 bedroom/4.5 bath home services from small to a larger family of 8 . Has it own private salt water pool, ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

4 Bedroom 2 bath home with private dock and private pool with direct open access to the ocean and convenient access to the bayside through Tavernier Creek. This is both family-friendly and a fisherman's dream. Our home sleeps 8 with every comfort you would want while on vacation in the keys...Large ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse located ...

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Property Type

Islamorada Townhome

"Lazy Daz Beac House"

Excellent couple to work with. Great communication. The rental was beautiful and clean. We had a problem with the rental and they communicated with us and together we solved the problem. They went over ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo ...

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Property Type

Islamorada Condo

"Great Home Away From Home!"

Perfect location! Our family had a great week and we will definitely come back. Condo is well furnished, clean and plenty of space. Kitchen is well stocked with essentials. Pool was very refreshing. The ...

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$166

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, pickleball, heated pool, private beach, and dockage for ...

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Property Type

Islamorada Condo

"What an EPIC stay in Islamorada"

Glenn's condo is the perfect place to get the breeze from the Gulf and the Atlantic side and his place is very nice and home like. Plenty of essentials to get right in and get your fishing or snorkeling ...

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3 BR | 2 BA | Sleeps 8 | Quick View

$372

avg/night

View Details

Key Amenities

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

About this property

Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,000 Lb boat lift in 2022. New paint inside and out 2022. New furnishings in 2022. White Marlin Beach access and quick boat ride to Channel 2 or 5 bridge or to Robbies Marina. Plenty of ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

Gorgeous updated 2 bedroom, 2 bathroom condo with large modern kitchen in an oceanfront gated building with oceanfront pool, fishing dock, gym, sauna, barbecue grills and so much more, and the best part is YOU'RE IN THE FLORIDA KEYS!

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Property Type

Islamorada Condo

"Jan Feb 2023"

Great condo, pool, and neighbors. Highly recommend. The pool is heated. Ocean view is great. Community room. Has exercise room and sauna.

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Key Amenities

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

About this property

Escape to paradise and experience the ultimate vacation getaway at our stunning 4-bedroom, 3-bathroom canal home in the heart of Islamorada. Nestled along the crystal-clear waters of the Florida Keys, this exceptional rental offers a perfect blend of comfort, convenience, and natural beauty.Key Features:Spacious ...

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Property Type

Islamorada House

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1 BR | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 1 miles to Anne's Beach

$200

avg/night

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Key Amenities

  • Air conditioning
  • Rentals by owner

About this property

Secluded Waterfront Apartment with Tiki hut, dock, King bed, 1 Bath, Sleeps 2.Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this ...

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Property Type

Islamorada Apartment

"Little piece of paradise!"

We stayed two weeks in the beautiful apartment and it was the best vacation ever! Chris is a wonderful host, very friendly and a wealth of information about the area! We will be back next year!

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1 BR | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 5 miles to Founders Park

$97

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Half Duplex HomeAre you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and manatees ...

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Property Type

Islamorada House

"Wonderful stay in the Keys!"

The screened in area and the outdoor space make this rental perfect! We kayaked on the canal, and walked around the neighborhood daily. We watched boats and manatees from the screened in porch. Lee (the ...

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$475

avg/night

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Key Amenities

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

About this property

This gorgeous, newly constructed, Islamorada home has 4-bedroom, 3+ bath and is located in the quiet neighborhood of Venetian Shores MM86. It provides immediate access to both the Atlantic Ocean and Florida Bay via Snake Creek.The deep-water dockage is ideal for the avid boater or fishing enthusiast. ...

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Property Type

Islamorada House

"Great Pool Rental!"

This was a great house! Our whole family enjoyed the stay very much. It was quiet and the layout of the home is perfect for multiple families to stay. The pool area was very nice and the dock is a perfect ...

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3 BR | 4 BA | Sleeps 8 | Quick View

Distance to beach: 0.5 miles to ANNE'S BEACH

$450

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the most beautiful crystal clear waters. The house is just minutes from Channel 5 and Channel 2 which give you quick access to the best ocean and backcountry fishing. You are ...

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Property Type

Islamorada House

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Key Amenities

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

About this property

This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.Upstairs ...

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Property Type

Islamorada House

"Perfection in paradise!"

This was a perfect house! Easy and quick access to ocean and gulf, docked 35’ boat right at the house, large pool with hot tub, plenty of parking for vehicles and trailers, very clean, well stocked, tiki ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Great house! Great location!HOUSE ON CANAL… 34 foot concrete dock with fish cleaning stand, water and electricity. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. We are also ...

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Property Type

Islamorada House

"Absolutely Perfect!"

The house was absolutely beautiful and perfect for bringing your boat. We had four adults and a one year old and the spacious home comfortably and easily accommodated us. Simple and easy access to Snake ...

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2 BR | 2 BA | Sleeps 4 | Quick View

$175

avg/night

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Key Amenities

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

About this property

Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking 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 Apartment

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean via Snake ...

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Property Type

Islamorada Condo

"Wonderful"

I highly recommend this vacation spot. Not only is the condo very nice the whole property is set up for your every need. The owner and property manager are very nice and accommodating. I was amazed by the ...

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5 BR | 3 BA | Sleeps 12 | Quick View

4

$657

avg/night

View Details

Key Amenities

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

About this property

Deam home in they keys is one of the very few legal weekly rentals in Islamorada. It is a 4000 square foot home on water with heated/chilled Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large ...

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Property Type

Islamorada House

"Amazing Family Vacation! Beautiful and affordable home in amazing location."

This was our first family trip to the FL keys and we had the most amazing time! Bridget was so helpful, especially since we booked prior to covid and decided to take our planned trip. She answered all my ...

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Islamorada Vacation Rentals