Islamorada Rentals
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 $253 per night (USD)Expedia
Islamorada Bungalows Suite 3
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Summary: Location is key! This beautiful and zen getaway is just minutes away from the Heart of Islamorada! The city's A ...
From $253 per night (USD)Expedia
From $300 per night (USD)VRBO
Islamorada Bungalows Suite 1 Bottom Floor
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Summary: Location is key! This beautiful and zen getaway is just minutes away from the Heart of Islamorada! The city's A ...
From $300 per night (USD)VRBO
From $565 per night (USD)VRBO
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 $565 per night (USD)VRBO
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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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From $583 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 $583 per night (USD)VRBO
From $502 per night (USD)VRBO
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 $502 per night (USD)VRBO
From $562 per night (USD)Expedia
New Ground Level Caribbean Cottage
- Bedrooms:
- 2
- 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)Expedia
From $731 per night (USD)VRBO
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 $731 per night (USD)VRBO
From $1686 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 $1686 per night (USD)VRBO
From $2370 per night (USD)VRBO
Sensational Ocean Front Villa | Kayak+PBs+Cinema+Fire Pit+Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: This is a truly unique and spectacular Villa thanks to its breathtaking view of the sea and its warm sandy beac ...
From $2370 per night (USD)VRBO
From $458 per night (USD)Expedia
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 $458 per night (USD)Expedia
From $237 per night (USD)VRBO
Just Opened for February!...Remodeled Townhome in Resort Community...Book Now!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Guest who booked for years just cancelled due to illness so now this remodeled and luxurious 2 bed/2 bath townhome with ...
From $237 per night (USD)VRBO
From $301 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 $301 per night (USD)Expedia
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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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From $1023 per night (USD)Expedia
New! Pools~Dock~Bikes~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 $1023 per night (USD)Expedia
From $592 per night (USD)VRBO
ISLAMORADA BEACH HOUSE
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This stunning waterfront home is nestled in the exclusive Port Antigua neighborhood of Islamorada, Florida. Enjoy breath ...
From $592 per night (USD)VRBO
From $253 per night (USD)Expedia
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 $253 per night (USD)Expedia
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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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From $340 per night (USD)VRBO
Paradise in Islamorada Venetian Shores
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This home is a Key West style house that has plenty of space for the whole family. It boasts 3 bedrooms and 2.5 bathroom ...
From $340 per night (USD)VRBO
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 $478 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 $478 per night (USD)Expedia
From $731 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 $731 per night (USD)VRBO
From $731 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 $731 per night (USD)Expedia
From $267 per night (USD)VRBO
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 ...
From $267 per night (USD)VRBO
From $1744 per night (USD)Expedia
Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
King, Queen, 2 twins, 1 pullout. Custom designed and built from the ground up by resort owner Phil Sena with nothing ...
From $1744 per night (USD)Expedia
From $1744 per night (USD)VRBO
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 $1744 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
From $166 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 $166 per night (USD)Expedia
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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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From $553 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 $553 per night (USD)Expedia
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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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From $226 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 $226 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
From $483 per night (USD)Expedia
Tropical Oasis private home w\/ office. NO STAIRS! Pet friendly, family friendly!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This newly renovated, 3/2 pet-friendly Tavernier vacation home is spaciously laid out with chic island-interior finishes ...
From $483 per night (USD)Expedia
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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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From $562 per night (USD)Expedia
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)Expedia
From $675 per night (USD)VRBO
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 $675 per night (USD)VRBO
From $630 per night (USD)VRBO
Better Choice For Your Vacation, Near History of Diving Museum, Pets are Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $630 per night (USD)VRBO
From $1443 per night (USD)VRBO
Create Memories w\/ Fun-filled Adventures at this Paradise! Near Sea Oats Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1443 per night (USD)VRBO
From $1415 per night (USD)VRBO
Best Value, Quality Stay with Free Parking, Near Islamorada Brewery & Distillery
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1415 per night (USD)VRBO
From $992 per night (USD)VRBO
High Tides and Good Vibes! 2 Relaxing Units, Pet-friendly Property, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $992 per night (USD)VRBO
From $1205 per night (USD)VRBO
A Place You'll Surely Enjoy! 3 Comfortable Units, Onsite Pool, Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $1205 per night (USD)VRBO
From $1491 per night (USD)VRBO
Short Distance From The Well Known Sites! 3 Family-friendly Units, Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $1491 per night (USD)VRBO
From $807 per night (USD)VRBO
Relax and Recharge! 2 Comfortable Units, Free Parking, Onsite Swimming Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $807 per night (USD)VRBO
From $307 per night (USD)VRBO
Best Place to Unwind! Free Parking, Pet-friendly Property, Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $307 per night (USD)VRBO
From $558 per night (USD)Expedia
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)Expedia
From $417 per night (USD)VRBO
Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, 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 $417 per night (USD)VRBO
From $417 per night (USD)VRBO
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 $417 per night (USD)VRBO
From $367 per night (USD)VRBO
Beautiful Upper Unit with Dockage, Pool and Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY NAME: Parrot Eyes 130 Plantation Ave. Tavernier, Florida 33070 LOCATION: Bayside Canal home located in Taverni ...
From $367 per night (USD)VRBO
From $635 per night (USD)Expedia
Beautiful Home with Dockage, Pool and Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
PROPERTY NAME: Parrot Eyes 130 Plantation Ave. Tavernier, Florida 33070 LOCATION: Bayside Canal home located in Taverni ...
From $635 per night (USD)Expedia
From $742 per night (USD)VRBO
Venetian Shores 5bed 7b, Pool , Spa, Boat lifts, open for Oct 2024
- Bedrooms:
- 8
- Bathrooms:
- 5
- Sleeps:
- 10
September 2024 special 40% discount 5 bedroom 7 bath in Venetian shores in the Florida Keys, Pool and Hot Tub with a hu ...
From $742 per night (USD)VRBO
From $289 per night (USD)Expedia
Ocean View Delight | Sea Gulls 310 ~ Monthly Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Best View in the Keys - You will feel right at home in this beautifully renovated condo with FULL OCEAN VIEW. T ...
From $289 per night (USD)Expedia
From $257 per night (USD)VRBO
Sandy Toes Await At This Beach Front Sandy Point Condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect beachside retreat! Discover the epitome of relaxation and luxury in our meticulously renovated m ...
From $257 per night (USD)VRBO
From $343 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 $343 per night (USD)VRBO
From $509 per night (USD)VRBO
La Casita White Marlin
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to this stunningly renovated 5-bedroom, 3-bathroom home situated on a picturesque canal, offering a seamless ble ...
From $509 per night (USD)VRBO
From $426 per night (USD)Expedia
Mojito Breeze Getaway by RedAwning
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to your tropical paradise in Tavernier, Florida! This stunning vacation rental is a slice of heaven nestled in t ...
From $426 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 $513 per night (USD)VRBO
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 $513 per night (USD)VRBO
From $582 per night (USD)VRBO
Ensuring a Very Comfortable & Memorable Stay, Near History of Diving Museum
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $582 per night (USD)VRBO
From $232 per night (USD)Expedia
This condo is located in one of Islamorada's most prestigious condo complexes.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY NAME: Beacon Reef #307 83201 Old Highway, Islamorada, Florida LOCATION: Ocean side Condo MINIMUM STAY: 28 Day ...
From $232 per night (USD)Expedia
From $340 per night (USD)VRBO
Beautifully remodeled roomy single family stilt home,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
PROPERTY NAME: West Plaza 63 West Plaza Del Lago, Islamorada, FL LOCATION: Bayside House MINIMUM STAY: 28 Days, All s ...
From $340 per night (USD)VRBO
From $680 per night (USD)Expedia
Boaters Paradise - Luxury Islamorada waterfront home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stunning waterfront Islamorada house on a corner lot with direct access to the Bay and 5 minutes from the Atlantic Ocean ...
From $680 per night (USD)Expedia
From $448 per night (USD)VRBO
\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the ...
From $448 per night (USD)VRBO
From $624 per night (USD)Expedia
Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
PROPERTY NAME: Pelican Landing 60 West Plaza Del Lago, Islamorada, FL LOCATION: Bayside Private Home in the neighborhoo ...
From $624 per night (USD)Expedia
From $558 per night (USD)VRBO
Ideal Mix of Comfort and Value! Near Islamorada Brewery & Distillery!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $558 per night (USD)VRBO
From $291 per night (USD)VRBO
Bayside Boater's Paradise-great for Snowbirds-28 d min stay- w\/ 1\/1private unit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This is a great home for your extended stay. It’s a 60 day minimum rental and we will give an additional discount if you ...
From $291 per night (USD)VRBO
From $1831 per night (USD)VRBO
Your Key to Unforgettable Island Moments! 2 Relaxing Units with Balcony!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1831 per night (USD)VRBO
From $410 per night (USD)VRBO
Your Retreat in the Heart of Islamorada! Kitchenette, Outdoor Swimming Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $410 per night (USD)VRBO
From $1838 per night (USD)VRBO
Whole House w\/ Tropical Atmosphere just Steps from the Beach - Ideal for Groups
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1838 per night (USD)VRBO
From $1412 per night (USD)VRBO
Embrace Nature by the Ocean! Beach, Swimming Pool, Full Kitchen!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1412 per night (USD)VRBO
From $722 per night (USD)VRBO
Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $722 per night (USD)VRBO
From $1078 per night (USD)VRBO
Relaxation at its Finest in Islamorada! Swimming Pool, Beach, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1078 per night (USD)VRBO
From $1868 per night (USD)VRBO
Beachside Bliss in Islamorada! Swimming Pool, Full Kitchen, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1868 per night (USD)VRBO
From $1182 per night (USD)VRBO
Your Majestic View in Islamorada! Swimming Pool, Kitchenette, Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1182 per night (USD)VRBO
From $649 per night (USD)VRBO
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)VRBO
From $413 per night (USD)Expedia
Port Antigua Canal Front Home & Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Get away on Island Time to beautiful Islamorada. Our home is in a lovely quite subdivision with the most beautiful priva ...
From $413 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
From $315 per night (USD)VRBO
BRAND NEW HOME and BOAT SLIP, pet friendly, resort location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This brand new home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean and ha ...
From $315 per night (USD)VRBO
From $400 per night (USD)VRBO
Waterfront w\/boat slip, New Construction
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Prime location for a relaxing stay, take in the views of the Atlantic from your private balcony. Two bedroom, two bath, ...
From $400 per night (USD)VRBO
From $400 per night (USD)VRBO
New Home, Waterfront, Boat Slip Included
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Brand new resort offering first class amenities, in the heart of Islamorada, near many restaurants, and across the stree ...
From $400 per night (USD)VRBO
From $332 per night (USD)VRBO
Private 2 Acre Bayside Waterfront Estate \n2\/2 All To Yourself ~ New Listing!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Private gated waterfront bayside property with an oceanfront 2 bedroom / 2 bathroom awaits you. This estate property o ...
From $332 per night (USD)VRBO
From $349 per night (USD)Expedia
3 Bedroom Home in Islamorada with Private Dock, Boat Ramp & private beach access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Visiting a house in Islamorada is a dream come true for those in search of the ultimate tropical paradise. Nestled in th ...
From $349 per night (USD)Expedia
From $507 per night (USD)VRBO
Gorgeous Keys Vacation Home in Prestigious Neighborhood of Port Antigua
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Beautiful Port Antigua waterfront home with a 60 foot concrete dock on a wide, clear-water canal. Access to Port Antigu ...
From $507 per night (USD)VRBO
From $223 per night (USD)Expedia
Ocean Islamorada BeachHouse POOL!70' DOCK boatrent
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Enjoy the keys life in style living in this beautifully furnished 2 Bedroom, 1 Bath, canal front retreat with r ...
From $223 per night (USD)Expedia
From $781 per night (USD)VRBO
The Salt & Light House Sleeps 24 dock, pool, beach
- Bedrooms:
- 4
- Bathrooms:
- 9
- Sleeps:
- 16
Summary: Sleeps 24 people across 7 bedrooms with 7 queen beds and 4 queen sofa beds Discover a rare gem in Islamorada, o ...
From $781 per night (USD)VRBO
From $558 per night (USD)Expedia
3 Lux Ensuites Walk\/Boat Island!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Dive into the heart of Islamorada and COUPLES Imagine: THREE MASTER BEDROOMS, so no squabbles over only 1 Maste ...
From $558 per night (USD)Expedia
From $219 per night (USD)VRBO
Bay Islamorada BeachHouse POOL!70' DOCK boat rent
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy the keys life in style living in this beautifully furnished or 2 Bedroom, 1 Bath, canal front retreat wit ...
From $219 per night (USD)VRBO
From $314 per night (USD)Expedia
Brand New Beach House 1st Floor W Pool Beach &Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: This listing is for the newly built 2020 downstairs of the duplex. You can Enjoy the keys life in style living ...
From $314 per night (USD)Expedia
From $339 per night (USD)VRBO
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)VRBO
From $3077 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 $3077 per night (USD)Expedia
From $452 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 $452 per night (USD)VRBO
From $1292 per night (USD)VRBO
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 $1292 per night (USD)VRBO
From $693 per night (USD)VRBO
Waves of Luxury: Access to Bayside Pool and Boat Slips. FREE Parking Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and b ...
From $693 per night (USD)VRBO
From $1074 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 $1074 per night (USD)VRBO
From $886 per night (USD)VRBO
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 $886 per night (USD)VRBO
From $790 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 $790 per night (USD)VRBO
From $212 per night (USD)VRBO
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 $212 per night (USD)VRBO
From $435 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 $435 per night (USD)VRBO