Islamorada, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Islamorada, Florida on RentalSaver.com!

Islamorada Rentals

From $118 per night (USD)
VRBO
Beautiful Efficiency Apartment - Bayfront, Islamorada Apt 232
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summer Sea Condominium Unit 232 is a brilliant, clean and modern efficiency apartment, newly upgraded in 2023 with tile ...
From $118 per night (USD)
VRBO
From $136 per night (USD)
Expedia
This studio makes the best of the space
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
This studio makes the best of the space. Living room by day bedroom by night with the convenient Murphy bed. All newly u ...
From $136 per night (USD)
Expedia
From $1381 per night (USD)
VRBO
New home with 95' of dock, pool with breathtaking Atlantic Ocean Views.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
New 4br/3bth home off Tavernier Creek, Ocean side with 95' of dock and lowered dock area for boarding kayaks and paddle ...
From $1381 per night (USD)
VRBO
From $146 per night (USD)
Expedia
Beautifully Updated Studio Apartment, Summer Sea Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This beautifully updated apartment is new to the rental market. Modern and clean with all the comforts of home, tropical ...
From $146 per night (USD)
Expedia
From $134 per night (USD)
VRBO
Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This beautiful modern Studio apartment has just been completely remodeled and new to the rental market. Every detail has ...
From $134 per night (USD)
VRBO
From $132 per night (USD)
Expedia
Beautiful Studio Apartment - Summer Sea Condo #230
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summer Sea Condominium Unit 230 is a brilliant, clean and modern efficiency apartment, upgraded with tile throughout and ...
From $132 per night (USD)
Expedia
$New 2\/1 Remodeled Cozy Home in Tavernier Key$
From $166 per night (USD)
VRBO
New 2\/1 Remodeled Cozy Home in Tavernier Key
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Relax at this peaceful and centrally-located 2/1 remodeled private home in Tavernier Key. Located near Tavernier Creek M ...
From $166 per night (USD)
VRBO
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Expedia
Charming 2 bed, 2 bath cottage 100 feet from private sandy ocean beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Charming fully furnished 2 bedrooms each with a king bed, 2 bath cottage just 100 feet from shared private sandy beach o ...
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Expedia
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VRBO
Beautiful oceanfront resort located at mile marker 73.8
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
We are committed to providing outstanding service and a great vacation experience to all of our guests. While Caloosa Co ...
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VRBO
From $1024 per night (USD)
Expedia
New~Pools~Dock~Bikes~3 King Beds~Kayaks~EV charger
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
There's a reason why we have ALL 5-star reviews! HeartofMorada is located in the HEART of Islamorada on Upper Matecumb ...
From $1024 per night (USD)
Expedia
From $740 per night (USD)
VRBO
Large Canal Front Family home in the heart of Islamorada
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Make yourself at home at this beautiful stay in Islamorada. Minutes away from the open ocean and the bay, this home is o ...
From $740 per night (USD)
VRBO
From $382 per night (USD)
Expedia
Oceanfront home ON Tavernier Creek
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This home is a fisherman's dream come true. New dock right on Tavernier Creek. You will be in open ocean in minutes!! ...
From $382 per night (USD)
Expedia
From $406 per night (USD)
VRBO
Large Waterfront Home with 80 ft Dockage and Boat Lift with Pool In Islamorada
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
80ft Dock and Boat Lift very close to Islamorada Sandbar and Alligator Reef. Great fishing, diving, snorkeling and boat ...
From $406 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Keys Cozy Townhouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy breathtaking sunset from your own private beach. Cottage nautical townhouse with your outside terrace. Best r ...
From $232 per night (USD)
Expedia
From $347 per night (USD)
VRBO
Gulf View Retreat @ Bay Harbor
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: 2/2 Bay harbor condo with stunning Marina and Ocean views! The Space: Escape to the breathtaking Gulf View Ret ...
From $347 per night (USD)
VRBO
From $276 per night (USD)
Expedia
A piece of Paradise in the Keys.
Bedrooms:
1
Bathrooms:
0
Sleeps:
5
Beautiful Canal Home in Florida Keys Islamorada. Amazing sunsets at our private beach just few blocks away. We have the ...
From $276 per night (USD)
Expedia
From $152 per night (USD)
VRBO
Beautiful Townhouse in the heart of the Florida Keys
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
SNOW BIRD.. COME TO PARADISE. 2/2 with a Loft (can be a 3rd bedroom) beautifully located in the heart of the Florida Key ...
From $152 per night (USD)
VRBO
From $505 per night (USD)
Expedia
Paradise Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautiful tranquil private beach is just the beginning of what awaits you in our completely renovated beach house. Port ...
From $505 per night (USD)
Expedia
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VRBO
Little Piece of Paradise (AVAIL Oct-Dec)
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Our Little Piece of Paradise is a relaxing place to enjoy with family and friends. We look forward to making it your hom ...
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VRBO
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Expedia
Islamorada Gem
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A completely renovated oceanfront townhome in beautiful Islamorada in the Florida Keys. 3 Story spacious 2 bedroom 2. ...
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Expedia
From $842 per night (USD)
VRBO
Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private 2acre Single Family Home awaits! Just another day in Paradise. Located at 75.7MM! Cozy, quiet, 3 bedroom (1 K ...
From $842 per night (USD)
VRBO
From $505 per night (USD)
Expedia
Beautiful Waterfront Port Antigua Home, Pool, Private Beach
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Stunning two-story, 3-bedroom resort-style, professionally decorated home. Inside, you'll find a modern and welcoming ho ...
From $505 per night (USD)
Expedia
From $739 per night (USD)
VRBO
Gulf access, private dock and private neighborhood beach!
Bedrooms:
1
Bathrooms:
5
Sleeps:
4
Recently updated Islamorada waterfront rental. Fully furnished and equipped kitchens! Come bring your boat or rent one t ...
From $739 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Islamorada Getaway in beautiful Port Antigua
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Stay in a beautiful home in one of the best communities in the Florida Keys- Port Antigua. You can sip a cocktail in you ...
From $408 per night (USD)
Expedia
From $2001 per night (USD)
VRBO
3 bedroom, 3.5 bath luxurious condo 402 at Maison in Islamorada
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Unit 402 of Maison Residences is an oceanfront and pool front property located on Old Highway. The 3 bedroom, 3.5 bath v ...
From $2001 per night (USD)
VRBO
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Expedia
Vacation Home in Paradise - Wonderful for Families
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Our house is situated in a quiet neighborhood close to the heart of Islamorada and the conveniences of Tavernier. This ...
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Expedia
$You will love my \Fl Keys Luxury Home\$
From $750 per night (USD)
VRBO
You will love my \"Fl Keys Luxury Home\"
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This tropical waterfront beauty has it all...heated pool, spa, dock, and custom elevator. It is well appointed and full ...
From $750 per night (USD)
VRBO
From $450 per night (USD)
Expedia
New Caribbean home. Resort access to pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 bedroom, 2 bath with 2 queen beds and 1 queen sleeper sofa. Sleeps 6. Does not include Boat Dockage or Daily Housekeep ...
From $450 per night (USD)
Expedia
From $562 per night (USD)
VRBO
New Ground Level Caribbean Cottage
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
2 bedroom, 2 bath with 1 king bed, 1 queen bed and 1 queen sleeper sofa. Sleeps 6. Boat dockage and Housekeeping NOT ava ...
From $562 per night (USD)
VRBO
From $788 per night (USD)
Expedia
Luxurious Caribbean 2 Bedroom 2 Bath Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled ston ...
From $788 per night (USD)
Expedia
From $403 per night (USD)
VRBO
Keys Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Two bedroom "gem" in the Florida Keys!! Enjoy our sand beach, beautiful sunsets, fish from our docks, swim in our pool, ...
From $403 per night (USD)
VRBO
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Expedia
Pristine Isalamorada canal front home with pool and boat dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This gorgeous waterfront house offers 3 bedroom/2 bath, pool & boat dock. The open floor plan of the main level is ideal ...
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Expedia
From $190 per night (USD)
VRBO
Perfect Family Summer Townhome at Club with Amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This spacious, fully remodeled 2-bedroom, 2-bathroom loft townhome is located in the heart of Islamorada at the exclusiv ...
From $190 per night (USD)
VRBO
From $592 per night (USD)
Expedia
ISLAMORADA BEACH HOUSE
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Luxury Waterfront Home in Exclusive Port Antigua – Islamorada, FL Escape to this stunning 4,200 sq. ft. waterfront retr ...
From $592 per night (USD)
Expedia
From $321 per night (USD)
VRBO
Spacious 3 bedroom home in Plantation key with 30 foot dock
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Make wonderful memories at this unique and family-friendly waterfront townhouse located on a deep-water canal with 30 fo ...
From $321 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Modern Cozy Beachouse Gem
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Elegant modern coastal gem! With beautiful canal views as well as incredible views of native area. Quiet, peaceful home ...
From $402 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Large Keys Home in Heart of Tavernier with 50 ft of deep water dock.
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Incredibly comfortable home located in the heart of Tavernier Key Mile Marker 90. Large home featuring incorporated do ...
From $293 per night (USD)
VRBO
$Charming oceanfront condo with pool, beach access, tennis, & washer\/dryer$
From $184 per night (USD)
Expedia
Charming oceanfront condo with pool, beach access, tennis, & washer\/dryer
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Escape to the Keys A6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $184 per night (USD)
Expedia
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VRBO
On the water in Islamorada elevated detached unit!!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Topsider resort is a unique water front property where all the units are elevated and detached featuring 2 bedrooms & 2 ...
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VRBO
$Islamorada retreat \Bungalow Blue\ w\/ heated pool, Bikes, BBQ, amenities galore!$
From $459 per night (USD)
Expedia
Islamorada retreat \"Bungalow Blue\" w\/ heated pool, Bikes, BBQ, amenities galore!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to paradise! Completely remodeled and immaculately maintained... Bungalow Blue is nestled away in the quiet qua ...
From $459 per night (USD)
Expedia
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VRBO
Beautiful estate nestled in a secluded cove on the ocean, 60 ft dock, guesthouse
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Meticulously maintained estate on the water with 60ft doc space and a lift. Incredible sunrises and sunsets from 3rd st ...
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VRBO
From $245 per night (USD)
Expedia
Serenity in Tavernier
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Beautiful 3/2 home in centrally located Tavernier! The Space: Escape to the enchanting Florida Keys – your tro ...
From $245 per night (USD)
Expedia
From $287 per night (USD)
VRBO
Gated canal-front retreat with pool water access, grill, AC & 2 kitchens
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Treasure Harbor Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $287 per night (USD)
VRBO
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Expedia
Exclusive Private ViLLA , Beach, Boat Ramp, Dock, Pool
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Enjoy Spectacular sunsets from property peninsula .Kayaking, snorkeling, beach, dock, boat ramp, Pool every thing you c ...
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Expedia
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VRBO
Tropical Vacation Home
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Quiet neighborhood located on a canal one block from the Atlantic Ocean. Home built in 2019, 2900 SF. Close to restauran ...
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VRBO
$Water-view house with private dock, washer\/dryer & grill - snowbird-friendly$
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Expedia
Water-view house with private dock, washer\/dryer & grill - snowbird-friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Two White Turtles Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
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Expedia
$Bungalow #4 - 2 Bed\/1 Bath & Pool in Islamorada$
From $478 per night (USD)
VRBO
Bungalow #4 - 2 Bed\/1 Bath & Pool in Islamorada
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, w ...
From $478 per night (USD)
VRBO
From $431 per night (USD)
Expedia
Malayan Palm East 1 Bedroom, 1 Bath Garden View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Poolside,1 Queen Bed,1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks a ...
From $431 per night (USD)
Expedia
From $785 per night (USD)
VRBO
Princess Palm South Poolside,1 King Bed, 2 FullBeds, 1 Pull Out
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Poolside,1 King Bed, 2 Queen Beds, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahog ...
From $785 per night (USD)
VRBO
From $788 per night (USD)
Expedia
Princess Palm North 2 Bedrooms, 2 Baths Poolside
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Poolside, 1 King Bed, 2 Queen Beds, 1 Pullout Resort guests stay in warm and inviting Caribbean-style homes. Rich mahog ...
From $788 per night (USD)
Expedia
From $1654 per night (USD)
VRBO
Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
King, Queen2 twins, 1 pullout. Boat Dockage Custom designed and built from the ground up by resort owner Phil Sena wit ...
From $1654 per night (USD)
VRBO
From $1647 per night (USD)
Expedia
Royal Palm North 3 Bedrooms, 3 Baths, Ocean Front,
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
King, Queen2 twins, 1 pullout. Boat Dockage Custom designed and built from the ground up by resort owner Phil Sena wit ...
From $1647 per night (USD)
Expedia
From $562 per night (USD)
VRBO
1 bedroom, 1 bath, full kitchen, 1 queen bed, 1 queen sleeper sofa.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 bedroom, 1 bath, full kitchen, 1 queen bed, 1 queen sleeper sofa. Welcome to The Bird of Paradise. This Ocean front h ...
From $562 per night (USD)
VRBO
From $623 per night (USD)
Expedia
Malayan Palm North 2 Bedrooms, 1 Bath, Garden View
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Poolside,2 Queen Beds,1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks ...
From $623 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Top Floor, Bay View, Dockage, Vacation Today!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come enjoy the breathtaking views this condo has to offer. Located in the Futura Yacht Club community, located at mile ...
From $215 per night (USD)
VRBO
From $528 per night (USD)
Expedia
New Rental! Beautiful canal pool home with dockage!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Cozy, canal front, pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Ba ...
From $528 per night (USD)
Expedia
From $558 per night (USD)
VRBO
Waterfront Luxury Bayside Home, Maritime Modern
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
There is something for everyone in your group within reach. If you are a boater, the open bay is only a moment's boat ri ...
From $558 per night (USD)
VRBO
From $2794 per night (USD)
Expedia
Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Pineapple Beach is situated on more than 3 acres in the central area of Islamorada. This exclusive 5-bedroom luxury resi ...
From $2794 per night (USD)
Expedia
From $422 per night (USD)
VRBO
House in Islamorada, in exclusive Venetian Shores.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The moment you step inside this calming retreat in exclusive Venetian Shores you feel on vacation with permanently assig ...
From $422 per night (USD)
VRBO
$Breathtaking Bayfront Villa w\/ Private Patio & Living Area, Perfect For Couple$
From $955 per night (USD)
Expedia
Breathtaking Bayfront Villa w\/ Private Patio & Living Area, Perfect For Couple
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $955 per night (USD)
Expedia
$Stunning Bay View Villa in Florida Keys | Beach Getaway w\/ Scenic Outdoor Pool$
From $791 per night (USD)
VRBO
Stunning Bay View Villa in Florida Keys | Beach Getaway w\/ Scenic Outdoor Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $791 per night (USD)
VRBO
From $609 per night (USD)
Expedia
Picture-Perfect Villas Offering Pool Relaxation & Ocean Adventures Nearby
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $609 per night (USD)
Expedia
$Waterfront Escape: Bayfront Accommodation w\/ Kitchen, Onsite Pool, Free Parking$
From $551 per night (USD)
VRBO
Waterfront Escape: Bayfront Accommodation w\/ Kitchen, Onsite Pool, Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $551 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Gorgeous Canal front home with a pool and Tiki hut
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly furnished 3 BR / 2 Bath . Minutes from Bay & Ocean Make yourself at home in a newly furnished 3 bedroom, 2 bath ho ...
From $203 per night (USD)
Expedia
From $571 per night (USD)
VRBO
Turquoise Escape - Newly renovated Canal home with heated pool and dockage.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Boaters Paradise! Pet Friendly Bayside pool home - minutes to open ocean through Tavernier Creek. 50' dock with power ...
From $571 per night (USD)
VRBO
$Condo on Islamorada on the beautiful Atlantic Ocean.\nCome enjoy and relax!$
From $170 per night (USD)
Expedia
Condo on Islamorada on the beautiful Atlantic Ocean.\nCome enjoy and relax!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Wake up and enjoy sunrise on the pier over the Atlantic and walk across the street at night and watch sunset on the Gulf ...
From $170 per night (USD)
Expedia
$Superb Keys home w\/heated pool, jacuzzi, fast wifi & more!$
From $170 per night (USD)
VRBO
Superb Keys home w\/heated pool, jacuzzi, fast wifi & more!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Come, relax and enjoy yourself in the heated pool or jacuzzi at our home located on mm90 near shops & restaurants. This ...
From $170 per night (USD)
VRBO
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Expedia
Waterfront oasis with boat dock, amazing views, patio, & hammock - dog-friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gemstone Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
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Expedia
From $277 per night (USD)
VRBO
Lovely Oceanview 2 bedroom 2 bath home,with BOAT SLIP!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Home sits in the Sun Outdoors Islamorada Resort. Newer 2b/2b home w/ a boat slip within the private marina . Home has a ...
From $277 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Oceanview 2 bedroom, 2 bath home with a Boat slip in a pet friendly resort!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Home sits in the Sun Outdoors Islamorada Resort. New 2 bedroom 2 bath home with a boat slip within the private marina is ...
From $310 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Beachfront Cottage - Islamorada!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Immerse yourself in the tranquil beauty of this fully updated beachfront cottage in the heart of Islamorada. Enjoy the c ...
From $348 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Salty Suites, simply put, it's paradise 365 days a year.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Salty Suites is simply paradise 365 days a year. Located in the fishing capital of the Florida keys, Islamorada. This pe ...
From $289 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Starfish -1 bedroom 1 bath apartment with full kitchen in Islamorada, Florida.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Starfish is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are loca ...
From $222 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Newer Home in a Dog Friendly, ocean front resort.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This newer home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full two ...
From $275 per night (USD)
Expedia
From $148 per night (USD)
VRBO
Islamorada Condo with ocean access, monthly rentals only
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Month rentals only, no short term. $3,700 per month plus 12.5% tax and $100 cleaning fee. 2 bedroom 1 bathroom condo w ...
From $148 per night (USD)
VRBO
$Yolo \ You only live once\ - Fishing Paradise in Islamorada with a 70ft Dock!!!!$
From $339 per night (USD)
Expedia
Yolo \" You only live once\" - Fishing Paradise in Islamorada with a 70ft Dock!!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1440 sf - 2 Bedrooms king size bed in master bedroom with 2 queen beds in guest room (also includes xtra bed in guest ro ...
From $339 per night (USD)
Expedia
$2 Relaxing Bayfront Villa w\/ Private Patio | Scenic Bayside Resort$
From $1881 per night (USD)
VRBO
2 Relaxing Bayfront Villa w\/ Private Patio | Scenic Bayside Resort
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1881 per night (USD)
VRBO
$Bayside Tranquility: 2 Spacious Villa w\/ Private Patio | Onsite Pool$
From $1205 per night (USD)
Expedia
Bayside Tranquility: 2 Spacious Villa w\/ Private Patio | Onsite Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1205 per night (USD)
Expedia
$Bayside Tranquility: 3 Relaxing Villa w\/ Spacious Living Area & Kitchen$
From $1802 per night (USD)
VRBO
Bayside Tranquility: 3 Relaxing Villa w\/ Spacious Living Area & Kitchen
Bedrooms:
6
Bathrooms:
6
Sleeps:
18
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1802 per night (USD)
VRBO
$Capt Craig's 2 Bedroom\/1 bath Apartment in Tavernier, Florida Keys$
From $277 per night (USD)
Expedia
Capt Craig's 2 Bedroom\/1 bath Apartment in Tavernier, Florida Keys
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Capt. Craig’s Guest Quarters The Dolphin Suite is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami ...
From $277 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Newer Home, Resort Location, Ocean View
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This newer home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full two ...
From $280 per night (USD)
VRBO
$Scenic Resort w\/ Private Beach Access | Near History of Diving Museum, 3 Villas$
From $1802 per night (USD)
Expedia
Scenic Resort w\/ Private Beach Access | Near History of Diving Museum, 3 Villas
Bedrooms:
6
Bathrooms:
6
Sleeps:
18
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1802 per night (USD)
Expedia
From $552 per night (USD)
VRBO
Ultimate Vacation in Islamorada! Short Drive to Marathon International Airport
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $552 per night (USD)
VRBO
$Islamorada Getaway | 2 Family Ready Bayfront Villa w\/ Spacious Living Area$
From $1881 per night (USD)
Expedia
Islamorada Getaway | 2 Family Ready Bayfront Villa w\/ Spacious Living Area
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1881 per night (USD)
Expedia
From $955 per night (USD)
VRBO
Relaxing Bay Front Villa Ideal For Romantic Couple Beach Getaway | Free Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $955 per night (USD)
VRBO
From $609 per night (USD)
Expedia
Enjoy Sunset Views from Your Villa with Pool & Beach Access in FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $609 per night (USD)
Expedia
$Minutes to Library Beach Park! 2 Villa w\/ Living Area | Free Onsite Parking$
From $1492 per night (USD)
VRBO
Minutes to Library Beach Park! 2 Villa w\/ Living Area | Free Onsite Parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1492 per night (USD)
VRBO
From $169 per night (USD)
Expedia
Islamorada Condo in Highly Sought After Futura Yacht Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Futura Yacht Club is located at Mile Marker 88 bayside in the most desired part of the Florida Keys...Islamorada. Futur ...
From $169 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Futura Yacht Club Condo 403
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Warm up your cold weather blues with some Islamorada sunshine! This updated fourth floor condo can help you do just that ...
From $241 per night (USD)
VRBO
From $1992 per night (USD)
Expedia
Oceanfront Estate on Islamorada, Florida Keys - Ocean Oasis of Islamorada
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
It's an Ocean Oasis here on this beautiful estate in Islamorada! Over one acre right in front of your PRIVATE beach on t ...
From $1992 per night (USD)
Expedia
$Waterfront paradise with fire pit, Washer\/Dryer, and central AC$
From $244 per night (USD)
VRBO
Waterfront paradise with fire pit, Washer\/Dryer, and central AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Angler's Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $244 per night (USD)
VRBO
From $795 per night (USD)
Expedia
Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Escape to paradise in the heart of Islamorada, the fishing capital of the world! This stunning 4 bedroom home sleeps 8 ...
From $795 per night (USD)
Expedia
From $840 per night (USD)
VRBO
15% to 20% OFF LUXURY HOUSE CLOSE TO THE OCEAN IN PORT ANTIGUA
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Perfect vacation home for those who want to experience privacy and paradise in the Florida Keys! The house features plen ...
From $840 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Flakey's B&B in the heart of Islamorada
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
VR-284 A well established, extremely well maintained and family owned and operated vacation rental in the heart of Islam ...
From $285 per night (USD)
Expedia
From $251 per night (USD)
VRBO
Beautiful Waterfront Pool Home in the Best Location for Your Best Vacation!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Best Home to Share with Family and Friends! This Beautiful Home consists of two levels. The ground level has a 3bedrooms ...
From $251 per night (USD)
VRBO
From $649 per night (USD)
Expedia
Lush tropical plantings in a gated compound located directly on the Florida Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
PROPERTY NAME: Little Bay Cottage 82246 Overseas Highway, Islamorada, Florida LOCATION: Cottage located directly on th ...
From $649 per night (USD)
Expedia
From $286 per night (USD)
VRBO
Bayside Boater's Paradise-great for Snowbirds-60 d min stay- add 1:1private unit
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This 2 bedroom- 2 bath, fully-equipped kitchen waterfront home on a deep canal offers a 75 ft-wide frontage dock with 38 ...
From $286 per night (USD)
VRBO
$Venetian Shores 5BR\/7BA Home with Pool, Spa & Boat Lifts Available July & Aug 25$
From $784 per night (USD)
Expedia
Venetian Shores 5BR\/7BA Home with Pool, Spa & Boat Lifts Available July & Aug 25
Bedrooms:
8
Bathrooms:
5
Sleeps:
10
Rare Summer Openings! Your Private Resort Awaits in Islamorada We’ve just had a rare cancellation at one of our most s ...
From $784 per night (USD)
Expedia
From $424 per night (USD)
VRBO
Casa Ocasio: Waterfront bliss in the Florida Keys
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Come enjoy this beautiful home, located in the popular neighborhood White Marlin at mile marker 74.5. Perfectly situated ...
From $424 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Tropical Paradise Retreat in Islamorada! Pool, Pet-friendly, Free Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $361 per night (USD)
Expedia

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