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Islamorada Vacation Rentals

(115 rentals)
Islamorada House
Sleeps 8, 3 bedrooms, 3.5 bathrooms
36 reviews

Key Amenities

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

About this property

Welcome to Oasis4rent!Escape to 2.75 acres of private oceanfront paradise in the heart of Islamorada. Two beautifully appointed homes sit directly on the Atlantic with 200 feet of sandy beachfront, a heated saltwater infinity pool, and views of Alligator Reef Light on the horizon.The PropertyMain...

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$1,435
avg per night
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

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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Featured review

"Loved it."

We had great time. The weather was perfect and everyone there was friendly and help full. Also are host Nancy was very help full from start to finish. We did some great fishing in the gulf; everglades and...

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$196
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 2 bathrooms
18 reviews

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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Featured review

"The BEST spot in the Keys."

This rental is the best, starting with a great location, the homey feel, amazing hosts, and everything in between. The house is comfortable and has everything you need when travelling. Our daughter loved...

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$417
avg per night
Islamorada Estate
Sleeps 16, 7 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave of four charming cottages nestled in beautiful landscaping with a total of seven bedrooms and seven bathrooms. When entering through the gate you will feel a sense a tranquility that...

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$2,047
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 0.3 miles to White Marlin

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Guests at 253 Gulfview can safely launch their boat using the private boat ramp or dock the boat in deep water behind home on canal. Home has a screened-in porch, and covered parking. Fully renovated kitchen with new appliances. Large open concept living area with large dining table. 1st bedroom has...

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Featured review

"Great option"

John and Marie were great hosts and house was amazing. Recently remodeled and very comfortable. Dock fit my 30 ft center console perfectly.

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$454
avg per night

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Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Anne's Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

House, 3 Bedrooms, 2 Baths, (Sleeps 4-6)Spacious ground level home that will be easy on your legs--NO stairs to climb! The home is fully equipped with linens for the king, queen, and 2 double beds. The master bedroom has its own bath. A separate media room with a flat screen TV as well as a large...

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$330
avg per night
Islamorada House
Sleeps 10, 5 bedrooms, 5 bathrooms

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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$660
avg per night
Islamorada Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms
3 reviews

Key Amenities

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

About this property

Front-Row Ocean Views – A Location That Cannot Be ReplicatedWelcome to Paradise Palms—the crown jewel of the exclusive Peaceful Palms gated community. The luxe upgrade! Perfectly positioned just steps from the water, this newly built three-story home offers sweeping panoramic views and...

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Featured review

"Amazing Keys Vacation"

Paradise Palms was truly a paradise and Rebecca is the perfect host! Her oceanfront home was absolutely amazing; waterfront location, next to the pool, dock with amazing sunrise views over the ocean, every...

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$641
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Tucked away on a quiet street in Lower Matecumbe, this beautifully furnished canalfront home is everything you imagine when you think of a laid-back Keys escape. Surrounded by lush, tropical landscaping and offering total privacy, this 3-bedroom, 3.5-bath getaway has all the extras—100 feet of dockage,...

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$550
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 100 yards to Port Antigua Private Beach

Key Amenities

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

About this property

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 floor plan. There's a large...

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$239
avg per night
Islamorada Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The Artist's Cottage at Anglers Reef #136 - This beautiful home is located in Angler's Reef, a gated oceanfront community located in Islamorada. The owner has shared his own personal artwork throughout the unit for guests to enjoy. Angler's Reef is known for its beautiful tropical landscaping...

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$335
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

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

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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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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$278
avg per night
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 100 feet to Front door

Key Amenities

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

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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Featured review

"Pure serenity"

So clean, so quiet, so beautiful! My wife and I loved our stay at Ocean Harbour. Looking forward to next year!

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$181
avg per night
Islamorada House
Sleeps 8, 2 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle...

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$605
avg per night
Islamorada Cottage
Sleeps 5, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Green Cottage - The Green Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards...

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$463
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms
11 reviews

Distance to beach: 0.5 miles to White Marlin Beach

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 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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Featured review

"Villa Marlin Is the Whole Package"

We had a wonderful week in Islamorada at Villa Marlin. This property has everything you need for a water-focused time, especially a beautiful little beach. It was perfect for our grandsons who could have...

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$643
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

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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Featured review

"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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$187
avg per night
Islamorada House
Sleeps 14, 5 bedrooms, 4 bathrooms
1 review

Distance to beach: 3 miles to Founders Park

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to the Conch & Lobster Homes, a rare dual-home getaway located in the heart of Islamorada, just minutes from iconic Alligator Reef. Perfect for large families, multi-generational vacations, or group getaways, this tropical property comfortably sleeps up to 14 guests across two coastal designed...

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Featured review

"6/29 thru 7/6"

Both houses were great for our families. We will come again. Very close to everything you would want to do. Private drive and gates with access code. If I were to change anything it would be the...

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$877
avg per night
Islamorada Estate
Sleeps 12, 6 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an experience few can claim. Expansive terraces stretch across both levels, framing ocean views. This haven's open design and spacious rooms blend seamlessly with serene surroundings....

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$2,925
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Founders Park

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

*Discover Elevated Island Living at Sea Breeze 41 Luxury 3BR/2BA Condo with Private Boat Slip in Exclusive Coral Harbour Club, IslamoradaWelcome to Sea Breeze 41 — your personal slice of tropical paradise in the heart of the Florida Keys. Nestled within the highly coveted Coral Harbour Club,...

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$194
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
8 reviews

Key Amenities

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

About this property

Welcome to ‘The Beach House’ at Tarpon Point in Islamorada – This luxurious oceanfront home is in a private gated enclave of 12 houses. This home sits directly on ‘The Beach’. Being the end home, it is nestled next to lush mangroves and the ocean offering a lot more privacy....

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Featured review

"Fabulous place to stay!"

This unit on Islamorada provides wonderful oceanfront views. Our group included five retired women who all worked together in the past. We try to make a reunion vacation happen once a year. This is the...

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$624
avg per night
Islamorada Townhome
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to this laid-back, oceanfront townhouse in Angler's Reef, where coastal vibes and easy living come together in the perfect Keys getaway. With three bedrooms, three baths, and plenty of charm, this spot is all about kicking back and enjoying the island life.The space has a cool, beachy...

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$675
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

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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Islamorada Apartment
Sleeps 10, 5 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish captivating tranquility with a grand open-concept layout seamlessly blending living, dining, and a wet bar, all framed by panoramic seascapes, a chef's kitchen and access to top-tier...

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$707
avg per night
Islamorada House
Sleeps 8, 2 bedrooms, 2 bathrooms
6 reviews

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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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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$329
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Hot tub
  • Private pool

About this property

Welcome to Bay Harbour A-304, a waterfront penthouse in Islamorada featuring a private 50 feet deep water boat slip in a protected harbor with direct views of the marina and Atlantic Ocean. Atlantic Ocean views are visible directly beyond the protected harbor. Enjoy immediate Florida Bay access and quick...

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$386
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges the living area and gourmet kitchen with a grand terrace, all framed by uninterrupted ocean views. Bask in the heated pool, unwind on the covered patio, or step onto your private dock...

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$1,129
avg per night
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

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

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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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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$305
avg per night
Islamorada House
Sleeps 12, 6 bedrooms, 7.5 bathrooms

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

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • 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. The home accommodates up to 12 guests. Each suite can be rented individually or combined. Please note that there is no smoking and no pets.Sitting on an acre with 6 bedrooms, 7 and 1/2...

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$1,000
avg per night
Islamorada House
Sleeps 12, 5 bedrooms, 6.5 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Kara Pan - Islamorada's Premier Oceanfront Estate Home... Kara Pan 1. Discreet Key West style home is situated on a four-acre parcel surrounded by lush landscaping and a natural white sand beach dotted with palm trees. When entering the winding driveway, you will be intrigued with anticipation of...

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$2,071
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 0.5 miles to ANNE'S BEACH

Key Amenities

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

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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Featured review

"Perfect vacation home"

You could not ask for a more beautiful and clean vacation home. Everything seems really new and well kept. The moment you walk through the home you see the balcony with the beautiful view of the water....

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$425
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

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

Key Amenities

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

About this property

Book here and SAVE VRBO's $500-700 Booking fee for any stay!! PLUS our diect rates are the same or usually lower than on VRBO. Click on the "Link" to the left to see our many great reviews on our direct rental site.Welcome to Anglers Reef, a very special community of vacation homes....

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Featured review

"Great week in the Keys"

Our stay couldn't have been better. Great gated community beautifully landscaped, the house is great everything you could need. Very nice layout, Cold AC Great Pool just steps away, Location is exactly...

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$603
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

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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$632
avg per night
Islamorada Apartment
Sleeps 2, 1 bedroom, 1 bathroom
48 reviews

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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Featured review

"Best little slice of heaven!!"

This beautiful, perfectly maintained property was one of our best stays ever. This was our first time in Islamorada and we will be back. The accommodations were spotless, the patio, the view and the hammock...

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$200
avg per night
Islamorada House
Sleeps 10, 5 bedrooms, 4 bathrooms

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, BRING YOUR BOAT - dock with ocean-access...

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$1,718
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4 bathrooms
4 reviews

Distance to beach: 2 miles to Founders Park

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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Featured review

"The Home Had Everything and it all Worked"

This was the nicest home overall I have rented. If you have a boat, don't look elsewhere. Everything in the house functioned and the house had everything one would need, even for people who do cook while...

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$484
avg per night
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

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 BBQ, and tiki bar. Located...

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$200
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 3.5 bathrooms
2 reviews

Key Amenities

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

About this property

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and...

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Featured review

"Bayside Paradise Perfection"

Our family has been traveling to Islamorada for Spring Break for the last 4 years and this was by far our favorite place to stay! Our family enjoyed the private oasis that the townhome provided. We felt...

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$877
avg per night
Islamorada Condo
Sleeps 7, 3 bedrooms, 3 bathrooms
19 reviews

Key Amenities

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

About this property

Islamorada Vacation Rental | Private Dock, Oceanfront Pool & Sunrise ViewsStep off your back door onto a private dock in one of the Florida Keys' most sought-after vacation rentals. Hooked on Islamorada is a 3-bedroom, 3-bath oceanfront townhome in the gated Peaceful Palms community —...

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Featured review

"A perfect Islamorada getaway"

We had an absolutely wonderful stay in Islamorada! The property was perfect for our trip and gave us everything we were hoping for our family vacation. The home was comfortable, clean, and had plenty of...

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$513
avg per night
New
Islamorada House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

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

About this property

Gated Home | Dock, Heated Pool & 2 Pools | Pet-OK Welcome to HeartofMorada!Step into a private world in Islamorada's most coveted location. Heart of Morada sits in Coral Cove — a gated community of just 8 homes — giving you a private heated saltwater pool with waterfall, your...

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Islamorada House
Sleeps 8, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 0.3 miles to Anne's Beach

Key Amenities

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

About this property

Enjoy this modern and recently updated lagoon front 3 bed/3 bath single-family home on the Gulf side of Islamorada at MM 73.5, minutes from the Channel 2 and Channel 5 Bridges, offering immediate access to the oceanside of Lower Matecumbe Key. Dockage is available for up to a 35' boat, or use the...

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Featured review

"On a scale of 1-10 this property is a 12 overall !"

We have rented this property for 3 years and have been extremely pleased with all aspects from great hosts, nicely appointed house, heated pool, canal/dock access , easy out to ocean or bay, plenty of...

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$302
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Distance to beach: 0.5 miles to White Marlin Beach

Key Amenities

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

About this property

Bring your boat!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. Heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, and two floors facing the canal and a private sanctuary....

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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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$659
avg per night
Islamorada House
Sleeps 10, 4 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

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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Featured review

"It's like coming home!"

This is our third year at Blue Dorado. We love it here! Everything was perfect for our family. The access to the Ocean and Tavernier Creek is amazing. We saw so many beautiful sunrises and sunsets.

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$257
avg per night
Islamorada House
Sleeps 10, 4 bedrooms, 3 bathrooms
23 reviews

Key Amenities

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

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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Featured review

"Perfect Islamorada house for boating family"

House was perfect for us. Checked all the boxes, easy to access, great comfort throughout, dock perfect, fish cleaning station, pool was great. Ice machine, list goes on. We have rented from Islamorada...

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$475
avg per night
Islamorada Villa
Sleeps 14, 5 bedrooms, 4 bathrooms
2 reviews

Key Amenities

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

About this property

⭐ 5 bedroom 4 bathrooms (One bathroom by pool) ⭐ Canal home in Venetian Shores with access to bay and ocean ⭐ 100 foot of dockage on 100 foot wide deep canal. Ask about bringing your own boat ⭐ Location of canal is off Snake Creek near MM86 ⭐ Beautiful large pool with hot tub in tropical...

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$351
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms
3 reviews

Key Amenities

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

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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Featured review

"warm retreat"

Bay Harbor was delightful, from the condo unit to the grounds and amenities. We used the hot tub, exercise room and swimming pool, When we left there was 76 degrees, returned to 20 degrees in Pennsylvania.

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$397
avg per night
Islamorada House
Sleeps 10, 5 bedrooms, 4 bathrooms

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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$530
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

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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Featured review

"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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$500
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4 bathrooms
1 review

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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Featured review

"Bonefish at Tarpon Point 3 bedroom"

A BEAUTIFUL LOCATION. This was a well appointed house which made for a wonderful stay for three couples. The house is listed for rental as four bedroom four bath. In reality two king bedrooms with bath...

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$925
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
13 reviews

Distance to beach: 4 miles to Anne's Beach

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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Featured review

"Excellent location, wonderful ocean view with full sunrises, clean and well-equipped condo with large balcony."

Condo was well equipped and tastefully decorated in an appropriate style. Direct ocean views from a 50' balcony overlooking docked boots with the occasional manatee swimming by was exceptional. Location...

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$236
avg per night
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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°

FAQ

How many vacation rentals are there in/around Islamorada?

There are 115 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 $429.

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 59 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 41 oceanfront rentals in Islamorada available on FloridaRentals.com. Use our filters to search and book yours today!