Islamorada Vacation Rentals

(54 rentals)
Futura Yacht Club Bayside Condominium and Marina Dockage, Islamorada

$164

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed

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, ...

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Location Information

Islamorada, Florida,

Property Type

Condo

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Islamorada water front with free boat tie-up. Available weekly, Saturday to Sat

Islamorada water front with free boat tie-up. Available weekly, Saturday to Sat

1 BR | 2 BA | Sleeps 4 | Quick View

8

Distance to beach: 5 miles to Anne's Beach

$171

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Oceanfront
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner

About this property

The Osprey Nest (MM 82.3) is a private condo residence which is wonderfully maintained. It is the total upper floor of the building in the foreground. It is operated under FL DBPR license # MOT 5403060 and is inspected annually. This Non-Smoking home ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

"Mark and Dolly"
Reviewed July 15, 2018

Absolutely fantastic place to stay, we will definitely be back

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Luxury Home with Dock, Waterfall Pool, HotTub, Wi-Fi deep water dock up to 60 ft

$400

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Pet Friendly

About this property

Venetian Shores 4-Bed/4-Bath Luxury Pool Home with 100' Dock & Opt. ElevatorMINIMUM STAY: 29 DAYS Dreaming of a Florida Keys vacation where you can boat, fish, dive, snorkel, or stay home and swim in your own private heated pool? This is it. This ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly
  • No Pets Allowed

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 ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

"Worked at turkey point and Stayed at this condo"
Reviewed July 16, 2018

Loved it! Drive was about 45 minutes to work but seeing the ocean everyday after work was worth the drive.

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Pool Home Fisherman's Dream Ocean Side

$150

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed 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 (max) with every comfort ...

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Location Information

Islamorada, Florida, 33070

Property Type

House

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Ocean Breeze, at Bay Harbour

Ocean Breeze, at Bay Harbour

2 BR | 2.5 BA | Sleeps 6 | Quick View

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

About this property

“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much more.New to the Vacation Rental market, this 2 Bedroom condo at Bay Harbour has been outfitted to make a Statement. ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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DIRECT OPEN OCEANFRONT POOL HOME W/ Deep water 70ft dock, Saltwater Heated Pool

DIRECT OPEN OCEANFRONT POOL HOME W/ Deep water 70ft dock, Saltwater Heated Pool

4 BR | 3 BA | Sleeps 12 | Quick View

Owner special: Discounts for all stays. Inquire within

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Pet Friendly
  • Oceanfront
  • Kid Friendly
  • Non-Smoking

About this property

PLEASE INQUIRE WITHIN FOR ALL STAYS AND GOOD DEALS.OCEANFRONT Jewel in the Heart of Islamorada! This Open water home HAS IT ALL. Brand New (Sept 2017) Huge, heated salt water swimming pool, 70ft deep water dock (very rare for a open water home) with ...

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Location Information

Islamorada, Florida, 33070

Property Type

House

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Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$120

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Wheelchair Accessible
  • Waterfront
  • Beachfront
  • Oceanfront
  • Non-Smoking
  • No Pets Allowed

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 ...

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Location Information

Islamorada, Florida, 33036

Property Type

Apartment

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Beacon Reef 406 - Charming condo with lovely views of the ocean and pool.

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Pet Friendly
  • Beachfront
  • Oceanfront

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. "Beacon Reef 406" is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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Southern Diversion Islamorada

Southern Diversion Islamorada

5 BR | 3.5 BA | Sleeps 17 | Quick View

$857

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Beachfront
  • Oceanfront
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

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. ...

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Location Information

Islamorada, Florida, 33036

Property Type

Estate

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Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks & more

Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks & more

3 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.5 miles to White Marlin Beach

$457

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Oceanfront
  • Kid Friendly
  • Non-Smoking

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6Villa 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. It has three bedrooms, two bath, private home ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

"We'll Be Back!"
Reviewed August 11, 2018

I am SO glad I found this website and this house! After hours spent reviewing properties on other websites and then trying to ask questions through email, it was great to be able to talk directly to the ...

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Beacon Reef 522 - Oceanfront 5th floor (top floor) condo at Beacon Reef.

$147

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Oceanfront
  • Communal Pool

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. PHOTO UPDATES COMING SOON. "Beacon Reef 522" offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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Sunrise on Sunset

Sunrise on Sunset

3 BR | 3 BA | Sleeps 12 | Quick View

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Waterfront
  • Pet Friendly
  • Beachfront
  • Oceanfront

About this property

MINIMUM STAY: 28 DAYS “Sunrise on Sunset” is the ULTIMATE BEACH FRONT HOME. There are BREATH TAKING OCEAN VIEWS from almost every room in this house! Play in the sand, walk into the ocean or sit under the covered ground level area. ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Mitchell's Keys Villa - Private, Secluded House on the Bay

Mitchell's Keys Villa - Private, Secluded House on the Bay

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 5 miles to Five Miles

$185

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Waterfront
  • Pet Friendly
  • Oceanfront
  • Non-Smoking

About this property

Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a quiet residential area (rare). The villa is approx. 50 feet from the water. The property contains a wading beach and a free marina with ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Villa Riolo - Updated home and perfect for your next holiday in Islamorada

$117

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Pet Friendly
  • Kid Friendly
  • Non-Smoking
  • Managed by Property Manager

About this property

Minimum Rental: 28 Days"Villa Riolo" is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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The PERFECT Escape with pool & jacuzzi

$429

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Non-Smoking
  • No Pets Allowed

About this property

This beautiful 4 bedroom/ 4 bathroom home has a 60' dock directly behind the home . Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Florida Keys- Venetian Shores. Upstairs ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Sea Grape - Serene, quaint part of paradise that the entire family will enjoy..

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Pet Friendly
  • Beachfront
  • Oceanfront
  • Kid Friendly

About this property

*******THIS PROPERTY IS NOT CURRENTLY AVAILABLE FOR RENT*******MINIMUM STAY: 28 DAYSFABULOUS BEACH HOUSE located directly on a mile long sandy beach. The original "Sea Grape" was destroyed by Hurricane Irma in September 2017. ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Palms #405 - Totally Remodeled Condo with Ocean Views

$103

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Oceanfront
  • Kid Friendly

About this property

Minimum Rental: 28 Days"The Palms #405" is a diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip

$357

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Private Pool
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Free WiFi

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. ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Beacon Reef #310 - Beautiful condo with lovely views of the ocean.

$107

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

About this property

Minimum Rental: 28 Days"Beacon Reef 310" is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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Antigua Place - Charming vacation home located in Port Antigua.

$173

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Pet Friendly
  • Kid Friendly
  • Non-Smoking
  • Managed by Property Manager

About this property

MINIMUM RENTAL 1 MONTH: Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Beautiful Ocean Sunrise Views!

Beautiful Ocean Sunrise Views!

3 BR | 2.5 BA | Sleeps 6 | Quick View

3
LAST MINUTE DEAL 11/10 - 12/15: Weekly price reduction for remaining 2018 season!! Contact me via text:

$321

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Pet Friendly
  • Smoking Allowed
  • Communal Pool

About this property

Enjoy the sunrise over the Atlantic ocean or relaxing on a private, sunny lanai. Take a cruise around the many canals or out to Florida Bay to capture the sunset. A 30' boat slip is included with the rental. Beautifully furnished living spaces, large ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

"Beautiful Condo"
Reviewed August 15, 2018

We love Bay Harbour Condos! We've stayed in the community 3 times so far and this condo- WILL NOT DISAPPOINT. It's beautifully decorated and very spacious. Owners are sweet and communicate very well! We ...

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DEAL
Mitchell's Bayview Villa - Islamorada House on the Bay

$242

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Waterfront
  • Pet Friendly
  • Communal Pool

About this property

We have recently completed an inside and outside renovation. The Bayview Villa is a private, secluded villa facing Florida Bay and in view of the fabulous Everglades and gorgeous sunsets. Quick access to offshore fishing. Located in a lush tropical hammock ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

"Excellent -- perfect place to stay!"
Reviewed July 30, 2018

This property is amazing -- beautiful and spotless. If you are lucky enough to stay here -- you will appreciate the breathtaking view, gorgeous dock, perfect location and nicely furnished/decorated villa. ...

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W. Plaza del Lago - Promises to be a favorite!

W. Plaza del Lago - Promises to be a favorite!

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach

$133

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Waterfront
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager
  • Free WiFi

About this property

Minimum Rental: 28 Days"West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Little Bay Lower Duplex - Gated Bayfront Property Shared w/ 2 Other Rental Units

$357

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen

About this property

Minimum Rental: 7 DaysLittle Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Flamingo Cottage - Adorable 2 bedroom, 2 bath cozy cottage with pool.

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Kid Friendly
  • Non-Smoking
  • Managed by Property Manager

About this property

Minimum Rental: 28 DaysFlamingo Cottage is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Beacon Reef #222 - Gorgeous condo with panoramic views of the Atlantic Ocean.

$147

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Oceanfront
  • Kid Friendly

About this property

Minimum Rental: 28 Days"Beacon Reef 222" is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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Palms #407 - Beautiful condo with panoramic views of the Atlantic Ocean.

$97

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Oceanfront
  • Kid Friendly
  • Non-Smoking

About this property

Minimum Rental: 28 Days"The Palms #407" is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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Palms #214 - Lovely condo with panoramic views of the Atlantic Ocean.

$73

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

About this property

Minimum Rental: 28 Days "The Palms #214" is a gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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Matecumbe Jewel - 3 bedroom home with pool and dockage is a jewel of a home!

$150

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Pet Friendly
  • Kid Friendly
  • Non-Smoking

About this property

Minimum Rental: 28 Days"Matecumbe Jewel" is a jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Gulfview Getaway - Bayfront Home with Private Beach

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed

About this property

Minimum Rental: 28 Days"Gulfview Getaway" is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Palms #301 - Darling condo with panoramic views of the Atlantic Ocean.

$73

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Oceanfront
  • Communal Pool

About this property

Minimum Rental: 28 Days"The Palms #301" is an exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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Palms #309 - Exceptional condo with panoramic views of the Atlantic Ocean.

$82

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

About this property

Minimum Rental: 28 Days "The Palms #309" is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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Blue Water Retreat - Location!!!! Gorgeous house with Pool and Ocean Views.

$183

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Pet Friendly
  • Kid Friendly
  • Non-Smoking

About this property

Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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2 Master Bedrooms, Waterfront, Pool, Hot Tub, Gym/Tennis, Marina, Bikes, Jacuzzi

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

Condo is immaculate, has one of the best locations in the complex! FEELS LIKE YOU ARE LIVING RIGHT ON TOP THE WATER!!!Check out our (69) - 5 STAR REVIEWS on VRBO # 50672. FYI: This site does not charge you booking fees VRBO does.Fantastic Gated ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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Sunshine Place - Ground Level Unit with Ocean Views.

$171

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Pet Friendly
  • Oceanfront
  • Kid Friendly
  • Non-Smoking

About this property

Minimum Rental: 7 Days"Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

"Absolutely perfect!"
Reviewed November 16, 2018

My boyfriend and I stayed at The Sunshine Place to celebrate both of our November birthdays. I have been visiting the keys for many years and this is the best place I have found. The property was very ...

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BAYSIDE CONDO, MARINA, POOL AND BEACH * SPECIAL FALL DISCOUNT*

$114

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Free WiFi

About this property

Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental 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, ...

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Location Information

Islamorada, Florida, 33070

Property Type

Condo

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Brand New Waterfront Home with Pool and Dock

$450

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Kid Friendly
  • Non-Smoking
  • Managed 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 ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Dream Getaway in Islamorada at Anglers Reef

$350

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Beachfront
  • Communal Pool
  • Kid Friendly

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, ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Five Bedroom Pool home with Boat Slip in Marina..... Your Florida Keys Getaway!

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Non-Smoking

About this property

Welcome to paradise! This home is a new listing. If you are looking for a large beautiful home with a pool in a peaceful setting and in an absolutely perfect location for your stay in Islamorada, you have found it! We are located in Venetian shores off ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

1 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 4 miles to Founders Park

$214

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Pet Friendly
  • Non-Smoking

About this property

Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, ...

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Location Information

Islamorada, Florida, 33036

Property Type

Condo

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Island Conch Cottage

Island Conch Cottage

2 BR | 1.5 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.5 miles to Anne Beach

$125

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Pet Friendly
  • Kid Friendly
  • Non-Smoking
  • Managed by Owner

About this property

Island Conch Cottage A quaint ground level conch style cottage located at the end of a private street in a very quiet setting. Cottage and grounds have privacy fence and gate. The grounds are displayed as a sand beach setting. This property has 60’ ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

"Second time Around"
Reviewed September 29, 2018

This is the second time we stayed at this island conch Cottage, this is a beautiful home the neighborhood is very quiet and the locals are always friendly. We caught a variety of snapper just off the patio ...

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Keys Cottage; Remodeled Villa in Native Hammock on Florida Bay

$214

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Pet Friendly
  • Non-Smoking
  • Managed by Owner
  • Free WiFi

About this property

The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely ...

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Location Information

Islamorada, Florida, 33036

Property Type

Cottage

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New Interior, Oceanfront End Unit, Pool, WiFi, Great Ocean Views

New Interior, Oceanfront End Unit, Pool, WiFi, Great Ocean Views

2 BR | 2 BA | Sleeps 5 | Quick View

1

Distance to beach: 1 miles to Harry Harris

$136

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Beachfront
  • Oceanfront
  • Communal Pool

About this property

Lovely 5th floor end unit right on the Atlantic Ocean in a peaceful neighborhood. Oceanfront clean heated pool and private covered parking space. WiFi included. Sandy beach area.Convenient to the main land and many things to do. Elevators take ...

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Location Information

Islamorada, Florida, 33070

Property Type

Condo

"Great Views, Comfortable Condo, Great Bargain!"
Reviewed September 9, 2018

My wife and I stayed here the first week in September, 2018 and wouldn't you know it, we got a tropical storm! It was just one rainy day however. This condo is on the 5th floor of a 7 story building, ...

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Paradise in Islamorada

Paradise in Islamorada

2 BR | 2.5 BA | Sleeps 6 | Quick View

$300

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

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, ...

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Location Information

Islamorada, Florida, 33036

Property Type

Villa

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Waterfront Paradise with Free Dockage - Contact us to price your stay!!

Waterfront Paradise with Free Dockage - Contact us to price your stay!!

1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 12 miles to Founders Park

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Waterfront
  • Oceanfront
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Free WiFi

About this property

Secluded Waterfront Studio 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 you have a minimum of 28 days entered in your contact form! We do not use the ...

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Location Information

Islamorada, Florida, 33036

Property Type

Studio

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Islamorada 3/2 Canalfront with Pool and Dockage

Islamorada 3/2 Canalfront with Pool and Dockage

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2000 feet to White Marlin

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Pet Friendly
  • Beachfront

About this property

Come visit Islamorada and enjoy a solar heated pool with Jacuzzi! You will also have access to a private homeowner's sandy beach! The sunsets are incredible! Come to paradise and relax in this Islamorada 3/2 with dockage. Bring your boat; you are just ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

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Islamorada Paradise Vacation Home on the Water

$229

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • Managed by Owner

About this property

Great house! Great location!House On Canal… 60 foot concrete dock with fish cleaning stand, water, electricity and dock ladder. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and ...

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Location Information

Islamorada, Florida, 33070

Property Type

House

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Pool Home - Fisherman's Dream and Wife and Kids Will Love it!

$167

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager

About this property

This beautifully furnished waterfront home with ocean views will thrill the most ardent diver or fisherman and his family. You will love the luxury of a heated pool, magnificent view, and protected deep water dockage for multiple boats. It is located on ...

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Location Information

Islamorada, Florida, 33036

Property Type

House

"July Vacation"
Reviewed August 6, 2018

We enjoyed the home and our vacation. We encountered some problems that were taken care of and some that were not the fault of owner or management company. The dock was damaged by hurricane Irma and was ...

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Osprey Lagoon Half Duplex House, 28 night minimum

$67

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

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 ...

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Location Information

Islamorada, Florida, 33070

Property Type

House

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Islamorada Vacation Rentals

Local 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°

The “Village of Islands” awaits you: Islamorada vacation rentals by owner


Sunny, friendly Islamorada is a smart choice for those who want a quiet escape away from the hustle and bustle of the major Florida hot spots. Located between Mile Marker 91 and Mile Marker 74, Islamorada is situated halfway between Miami and Key West along Florida’s scenic Route 1. Islamorada itself is spread out over six islands, each surrounded by tranquil ocean and soft sands.

Next time you’re looking for fun & sun, skip the traditional beachside hotel and opt for a vacation rental in Islamorada instead from FloridaRentals.com. When staying in a beach condo instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our rentals even come with special amenities like a backyard pool, washer/dryer units, and bicycles. Whether you’re looking for a super-sized modern villa with an indoor pool, or a cozy beachfront bungalow, you can find it on our site.

Islamorada, Florida travel advice


This destination is a tropical paradise for those looking to get away from it all. In fact, celebrities have made the secluded Islamorada a second home for decades, including the island’s most famed resident, baseball player Ted Williams. Be careful, or you might just fall in love with the area, too.

With a tropical climate and daytime temperatures that rarely dip below the 70s (F), Islamorada is a fantastic vacation spot any time of the year. During the summer, temperatures typically hover in the upper 80s. The ocean breeze cools temps down in the afternoon, and the conditions are just perfect for fishing (more on this below).

Getting here from Miami International Airport or Key West Airport is easy with a rental car, and the views on Route 1 and connecting bridges are incredible. Worth the drive! Once you’ve arrived, island hopping via boat is a fun way to see the entire area.

Named by early Spanish explorers, Islamorada literally translates to “purple isles” – a nod to the colors one might see during one of the legendary sunsets.

Top activities and attractions


The sport fishing capital of the world, this city offers activities for anglers of all ages and skill levels. The surrounding ocean and shallow bays teem with a variety of fish, including sailfish, bonefish, swordfish, marlin and tarpon. Hop aboard a deep sea fishing charter to try your hand at grabbing one of these fish and cooking your own catch for dinner. If you’d rather stay on land, explore try fly fishing in the backcountry.

Fishing not your thing? That’s fine, there’s plenty of other activities in the area. Grab a towel and head to Anne’s Beach for a full day of sand castles and snorkeling. It’s also private and quiet, so you will feel a long way away from the crowds on South Beach. If you’re feeling adventurous, try your hand at kite surfing since the shallow waters here provide an ideal environment.

Bring your family to the Theater of the Sea and take a live snorkeling tour or swim with dolphins. If you prefer nature surroundings, Windley Key Fossil Reef Geological State Park has nature trails for hiking. Don’t miss the underwater shipwreck site at San Pedro Preserve where scuba divers love the scenery and adventure.

Music lovers enjoy warm, tropical evenings and daylong music festivals on the lawn of the outdoor, waterfront ICE Amphitheater located inside Islamorada Founders Park, a 40-acre expanse that features an Olympic-sized pool, shallow water beach, water sports rentals, ball fields, fishing jetty, exercise opportunities, skatepark and a dog park.

Dining


Known for delicious seafood, Islamorada’s restaurants serve up the day’s freshest catch. Starting at breakfast, stop in to the Midway Cafe & Coffee Bar where guests can start their day off with an omelette or pancakes. For lunch, grab a wrap at Chef Michael’s where they feature daily seafood dishes that “wow” eaters. Want to eat with a view? Grab an outside table at Morada Bay and watch the palm trees sway as you grub. Lastly, the Green Turtle Inn has more seafood dishes and soups that come with rave reviews.

Islamorada homes for rent on FloridaRentals.com


Islamorada condo rentals on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!