Islamorada Rentals
From $222 per night (USD)VRBO
Beautiful centrally located home in the Florida keys<br>
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Centrally located in the Florida keys close to Islamorada where there are great restaraunts and shops.Park your boat in ...
From $222 per night (USD)VRBO
From $572 per night (USD)VRBO
A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
''BEAUTIFUL BAY-FRONT PROPERTY!!!!'' NEW POOL Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. T ...
From $572 per night (USD)VRBO
From $1032 per night (USD)VRBO
You will never want to leave
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This Ocean Retreat offers breathtaking views from every room, with a 60' covered balcony that overlooks the 32' Pool/Spa ...
From $1032 per night (USD)VRBO
From $351 per night (USD)Expedia
Anglers Reef Islamorada, Bikes,Kayak,Paddle Boards DOCK available-Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
112 Anglers Way Islamorada Village vacation rental #24-0371 Call me for more information 305-240-0592. (2 houses side b ...
From $351 per night (USD)Expedia
From $1647 per night (USD)VRBO
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Spectacular property - two stories of true keys paradise in a relaxed basin-front setting. Newly renovated, the proper ...
From $1647 per night (USD)VRBO
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Long Term Rental Upper Keys Bayside Condo w/ boat slip & easy access to Atlantic
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fully renovated two bedroom condo in the Upper Keys. Fabulous views of Florida Bay and community pool with private slip ...
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From $374 per night (USD)VRBO
Oceanfront home ON Tavernier Creek
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This home is a fisherman's dream come true. New dock right on Tavernier Creek. You will be in open ocean in minutes!! ...
From $374 per night (USD)VRBO
From $841 per night (USD)VRBO
The Beach House-Luxury Oceanfront Home, Unobstructed Views, Pool, Sandy Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
‘The Beach House’ at Tarpon Point in Islamorada-OWNER DIRECT RENTAL WITH NO ADMIN OR CC FEES ‘The Beach House’ is a lux ...
From $841 per night (USD)VRBO
From $390 per night (USD)VRBO
Tavernier Keys Home w/ 70’ Dock & 20k Boat Lift on Bayside! 3/2.5 Plus Game Room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Gorgeous and Spacious Bayside Tavernier Keys Home with a 70’ foot Dock for your Boat and 20,000 lb Boat Lift. Be in the ...
From $390 per night (USD)VRBO
From $452 per night (USD)Expedia
Islamorada Anglers Reef! “Sandbar Bungalow Villa\" AMAZING! Middle row location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
AMAZING MIDDLE ROW! COMPLETELY UPDATED! BOAT SLIP AVAILABLE This oceanfront resort is a boutique complex of 52 homes ins ...
From $452 per night (USD)Expedia
From $805 per night (USD)VRBO
Bay Front Home With Magnificent Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Islamorada, the fishing capital of the world, this house is tucked away in a quite neighborhood on the bay si ...
From $805 per night (USD)VRBO
From $355 per night (USD)Expedia
Stunning Keys home w/pool, jetted tub, elevator & more!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Paradise. Come and relax in our Bayside home and enjoy the coastal breeze and rustling palms in your own pri ...
From $355 per night (USD)Expedia
From $415 per night (USD)VRBO
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths ...
From $415 per night (USD)VRBO
From $210 per night (USD)Expedia
SPECTACULAR SUNSETS AND FRESH OCEAN BREEZE AWAIT YOU IN ISLAMORADA, FLORIDA!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just under 1.5 hours from Miami International Airport, you will find the beautiful gated community of Executive Bay Club ...
From $210 per night (USD)Expedia
From $734 per night (USD)VRBO
Island pool home awaits in Islamorada's Port Antigua
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your island pool home awaits in Islamorada's Port Antigua! 3,500 square foot, 4 bedroom, 3 bathroom, high ceilings, til ...
From $734 per night (USD)VRBO
From $454 per night (USD)VRBO
Islamorada waterfront retreat - private home w/heated pool, 30’ dock - 15% off
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
NOW OFFERING A SPECIAL RATE OF 15% OFF FOR BOOKINGS FROM SEPT. 2025 - DEC. 2025, Welcome to your private slice of ...
From $454 per night (USD)VRBO
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Pristine Isalamorada canal front home with pool and boat dock
- Bedrooms:
- 2
- 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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Venetian Shores Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Wonderful Keys home built and cared for by the same family since 1988. Located near MM 86, 2 hours from Miami, 2 hours ...
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From $193 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 $193 per night (USD)VRBO
From $1605 per night (USD)Expedia
3 acres Gated w/Beach,Pool,Bikes,Kayaks,EV charger
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper M ...
From $1605 per night (USD)Expedia
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Safety harbor seasonal fishing getaway with room for 12
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
Private fortress-like vacation home in coveted Safety Harbor Lower Matecumbe Key of the Village of Islamorada. 100 ft o ...
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From $809 per night (USD)VRBO
Ocean Front Contemporary Beach House, Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the sweet spot of the Florida Keys - Islamorada. Custom built and designed by an Award winning architect in 2 ...
From $809 per night (USD)VRBO
From $433 per night (USD)VRBO
Warm, sunny, perfect vacation in Islamorada's Anglers Reef
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 128 Anglers Way: "Morada Daydreaming". Our home away from home in the Angler's Reef exclusive gated community ...
From $433 per night (USD)VRBO
From $633 per night (USD)VRBO
Waterfront, Heated Pool, Spa & 15k lb Boat Lift: Express access to Ocean & Bay!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Fisherman's paradise! 70 feet of Canalfront with immediate access to ocean or bay and 15k pound boat lift. MINIMUM 28 N ...
From $633 per night (USD)VRBO
From $509 per night (USD)VRBO
Port Antigua South Islamorada Canal Front Home with Pool Dock & Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
SANCTUARY FOUND… At the intersection of two very wide sparkling canals sits this lovely, four bedroom, two and a half ba ...
From $509 per night (USD)VRBO
From $171 per night (USD)Expedia
Very Nice 3 Bedroom Home With Large Lot! Built to entertain! Boat Ramp!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This is a beautiful property that offers a home like atmosphere as well as complete privacy. The property is in the comm ...
From $171 per night (USD)Expedia
From $120 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 $120 per night (USD)VRBO
From $848 per night (USD)Expedia
Islamorada Happy Tarpon House: Heated Pool - Deep Water Boat Dock- Family Fun!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Happy Tarpon - The best of the Florida Keys. The best of Islamorada! Enjoy privacy in our beautifully renovated home in ...
From $848 per night (USD)Expedia
From $228 per night (USD)VRBO
Best Location for Your best vacation!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Best Home to Share with Family and Friends! This Beautiful Home consists of 2 levels with 2 separate units. The 1st leve ...
From $228 per night (USD)VRBO
From $293 per night (USD)VRBO
New saltwater pool, pet friendly, waterfront house with dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,0 ...
From $293 per night (USD)VRBO
From $407 per night (USD)VRBO
\"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!\"
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Discover the Keys from a unique perspective at this Islamorada rental home, a true haven for fishing enthusiasts! Positi ...
From $407 per night (USD)VRBO
From $1198 per night (USD)VRBO
Islamorada Paradise on Snake Creek
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Located directly on the water in fabulous Venetian Shores, Islamorada’s premier community. Our luxurious 5 bedroom/ 5. ...
From $1198 per night (USD)VRBO
From $365 per night (USD)VRBO
Casa Del Pirata / 3 bed / 2 ba Canal Home in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Casa Del Pirata! Located in the heart of Port Antigua, this canal front home boasts tropical vibes and can ...
From $365 per night (USD)VRBO
From $226 per night (USD)Expedia
Islamorada Lovely Panoramic Ocean VIEWS! Oceanfront Corner Condo, Pool, More!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FOR VIEW LOVERS and a favorite of returning visitors. EVERY ROOM has a gorgeous OCEAN view. This totally renovated, Is ...
From $226 per night (USD)Expedia
From $1493 per night (USD)VRBO
Oceanfront 165ft Beach-Dock-Pool-4K sq.ft 4 bed-5 bath - Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Islamorada Rental License: VR - 065 *** SATURDAY TO SATURDAY RENTALS ONLY! If your preferred dates are not available, ...
From $1493 per night (USD)VRBO
From $202 per night (USD)Expedia
Canalfront, Dog-Friendly Home with High-Speed WiFi, Private Boat Ramp, and Kayak
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Islamorada Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $202 per night (USD)Expedia
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Beautiful Beach Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our beach house located in the heart of Islamorada. Just a short drive from the best restaurants, bars, state ...
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From $518 per night (USD)VRBO
Venetian Shores Home -DOCK remodeled 3/3 POOL/Hot Tub! Deep water Dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
126 Palermo Drive Check out this new to the Vacation Rental Market home in Venetian Shores on canal with 70' dock, pool, ...
From $518 per night (USD)VRBO
From $241 per night (USD)VRBO
Idyllic Tropical Paradise Overlooking the Fabulous Florida Bay.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This condo is located in your tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yac ...
From $241 per night (USD)VRBO
From $551 per night (USD)VRBO
Waterfront Community Townhome with Marina, Beach and a Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SPRING SPECIAL: SAVE 20% When You Book Between April-June! Take your dream Keys vacation in this spacious 3bd/2bth wate ...
From $551 per night (USD)VRBO
From $582 per night (USD)VRBO
You will love my \"Fl Keys Luxury Home\"
- Bedrooms:
- 3
- 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 $582 per night (USD)VRBO
From $731 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 $731 per night (USD)Expedia
From $291 per night (USD)VRBO
Islamorada beach house - PRIVATE BEACH - KAYAKS - DOCK SPACE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the Florida Keys from our newly renovated home in a quaint neighborhood located in Islamorada. This 2 bedroom, 2 ...
From $291 per night (USD)VRBO
From $319 per night (USD)Expedia
Water Front 3/3 Family and Boat Friendly Home, Great Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful well-kept and spacious two story bay-side waterfront home is a perfect rental home for you and your famil ...
From $319 per night (USD)Expedia
From $473 per night (USD)VRBO
Tropical Keys Retreat – Fully Furnished 3 Bed, 3 Bath Waterfront Gem. Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your ideal getaway in the heart of the Florida Keys! This beautifully furnished two-story, 3-bedroom, 3-bath ...
From $473 per night (USD)VRBO
From $1350 per night (USD)Expedia
4 Bedroom Private Oceanfront House - Bahia
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 4 bedroom private oceanfront house overl ...
From $1350 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 $1941 per night (USD)VRBO
Stunning Oceanfront Home located in Islamorada Florida
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
This stunning, completely renovated 5 bedroom, 6.5 bathroom home, sleeps 14 guests. Southwind sits on 1 acre of beachfr ...
From $1941 per night (USD)VRBO
From $679 per night (USD)VRBO
\" Endless Summer\" Awaits!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Sure you can drive another 1.5 hours to reach Marathon but why would you do that when the best restaurants and events ...
From $679 per night (USD)VRBO
From $413 per night (USD)Expedia
Florida Keys Luxury Houseboat, Unique living on the Water WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers ...
From $413 per night (USD)Expedia
From $1876 per night (USD)VRBO
Luxury home, Heated pool, Hot tub, Chefs kitchen, Sundeck, 100 ft of dockage.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
*** MINIMUM 28 NIGHT STAY *** Once you check-in, you’ll never want to leave 216 Johnny Road With quick ocean access, a ...
From $1876 per night (USD)VRBO
From $204 per night (USD)Expedia
Gated Community Townhome with Private Beach, Pool, and Tennis Courts!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Save up to 25% on all booking this year! Take your dream Keys vacation in this spacious 2bd/3bth waterfront town home i ...
From $204 per night (USD)Expedia
From $639 per night (USD)VRBO
Bayfront Home In Florida Keys
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy your stay at your own private oasis! You will approach this stunning home down a secluded road that leads into pa ...
From $639 per night (USD)VRBO
From $461 per night (USD)Expedia
Peacock Shores Islamorada - Vacation On The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The ocean is your front yard at this modern, luxurious townhome hidden away in a small, private seaside community. Enjoy ...
From $461 per night (USD)Expedia
From $415 per night (USD)VRBO
Canal Front Beautifully Renovated Home w/ Great Deck, Private Boat Ramp + WI-FI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This comfortable house, located in the quiet neighborhood of Plantation Key Colony, Offers three inviting bedrooms and 2 ...
From $415 per night (USD)VRBO
From $513 per night (USD)Expedia
NEW POOL ** Waterfront Paradise with Amazing Sunsets on Beach**
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra ...
From $513 per night (USD)Expedia
From $168 per night (USD)VRBO
Beautiful 2 bedroom Summer Sea Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful, modern, upgraded 2-bedroom, 1.5 bath apartment at Summer Sea has everything you would want for your fabu ...
From $168 per night (USD)VRBO
From $376 per night (USD)VRBO
Breezy Happy Hours in Port Antigua Beach Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This 2,500sf home has been completely renovated. With 4/3.5 this comfortable home is located in one of the most desirabl ...
From $376 per night (USD)VRBO
From $283 per night (USD)VRBO
Tavernier Creek - Plantation Key Home - 60' Dockage May & September Available!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to "Port of Call." The only thing missing is You and Your Boat! And You are in the premier location, just off Ta ...
From $283 per night (USD)VRBO
From $433 per night (USD)VRBO
Updated 3/2 condo Futura Yacht Club-Spacious Open Floor Plan, Sunset VIEWS!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Gorgeous completely remodeled spacious condo in the highly sought after Futura Yacht Club overlooking Florida Bay with s ...
From $433 per night (USD)VRBO
From $192 per night (USD)VRBO
Beautiful water front home, private dock in Islamorada, World Fishing Capital
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
This two-story house is located on an ocean access canal that is literally minutes from the Atlantic Ocean. Guest can do ...
From $192 per night (USD)VRBO
From $232 per night (USD)VRBO
Oceanfront condo in Islamorada, amazing sunrise views, renovated in 2019!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Watch the sunrise from your private balconies in both bedrooms overlooking the Atlantic ocean, and walk across the stree ...
From $232 per night (USD)VRBO
From $205 per night (USD)VRBO
Off the beaten path in one of Islamorada’s hidden gem of a community!.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Vacation like a local! This charming 2 bedroom, 2 bath home is located in one of Islamorada’s quaintest and quietest nei ...
From $205 per night (USD)VRBO
From $2880 per night (USD)VRBO
Open Ocean Views - 2 separate properties -House & Cottage With Dockage & Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
We privately own a total of 5 boutique vacation rentals in Islamorada: VRBO listing #1576833 (5 bedroom) VRBO listing #1 ...
From $2880 per night (USD)VRBO
From $263 per night (USD)VRBO
Key West Beachfront Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for the ultimate Florida Keys escape? Come enjoy the best boating in the Upper Keys! New Dock is now COMPLETE! ...
From $263 per night (USD)VRBO
From $739 per night (USD)VRBO
Private Cottage on Bayfront Estate – Pool, Beach, and Boating Paradise
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Garden View Cottage at Mermaid's Bay Boutique Estate, a serene hideaway located in the heart of Islamorad ...
From $739 per night (USD)VRBO
From $433 per night (USD)VRBO
Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This lovely oceanfront home is at Mile Marker 85 in exclusive An ...
From $433 per night (USD)VRBO
From $417 per night (USD)Expedia
New Construction home. 50' Dock w/ Pool & Hot Tub. Just S. of Tavernier Creek
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful Conch style home was completed in 2019. The house is a 2000 sq ft. 3 bedroom 2 bath home, each of it's 3 ...
From $417 per night (USD)Expedia
From $523 per night (USD)VRBO
NEW Luxury Modern Coastal Home in Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This New construction has all the bells and whistles to make your stay unforgettable. Located in the heart of Islamorada ...
From $523 per night (USD)VRBO
From $2408 per night (USD)VRBO
Oceanfront Estate with 4 Cozy Cottages
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave o ...
From $2408 per night (USD)VRBO
From $991 per night (USD)VRBO
Charming cottage on the Florida Bay in the heart of Islamorada with pool, dockage, beach + more
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Bay View Cottage is one of three private homes located at Mermaid's Bay Boutique Estate. Located in the heart of Isl ...
From $991 per night (USD)VRBO
From $122 per night (USD)VRBO
Modern one bedroom apartment with beautiful garden view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful, modern updated unit is absolutely beautiful with a private balcony with a wonderful garden view. Homey t ...
From $122 per night (USD)VRBO
From $380 per night (USD)VRBO
5 Star Modern Oceanfront Islamorada Townhome on the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Tw ...
From $380 per night (USD)VRBO
From $211 per night (USD)Expedia
Relaxing waterfront retreat with boat dock & amazing ocean views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $211 per night (USD)Expedia
From $433 per night (USD)VRBO
Oceanside Getaway: Renovated Home with Boat Slip, Pool & Beach - Gated community
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Palm La Mar, a luxury vacation rental located in the exclusive oceanfront gated community of Anglers Reef in Islamorada, ...
From $433 per night (USD)VRBO
From $204 per night (USD)Expedia
Florida Keys Chic
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy breathtaking sunsets from your very own private beach in this Florida Keys Chic townhome!!! Beautiful 3 bedroom 2 ...
From $204 per night (USD)Expedia
From $829 per night (USD)VRBO
Paradise Awaits!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful canal front Tavernier, FL home with minutes to the bay and easy ocean access through Tavernier Creek. Newly re ...
From $829 per night (USD)VRBO
From $432 per night (USD)Expedia
Waterfront Home in Islamorada with outdoor kitchen, pool, spa, boat dockage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Tut’s Cay located in Islamorada in the Florida Keys. Our home is centrally located in our favorite part of th ...
From $432 per night (USD)Expedia
From $445 per night (USD)VRBO
Mini Ray's of Sunshine
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Mini Ray's of Sunshine - Beautiful New Pool Home located in a gated community in the Heart of Islamorada. This home, des ...
From $445 per night (USD)VRBO
From $845 per night (USD)Expedia
Hidden Gem Duplex in Heart of Islamorada! Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: This truly is a Hidden Gem in the heart of Islamorada. Nestled in the trees just a few steps from one of the mo ...
From $845 per night (USD)Expedia
From $160 per night (USD)VRBO
Beautiful 1 bedroom apartment with stunning open water view Apt 317
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Premier 1 bedroom unit with both that stunning direct open water bay view and a view of the pool off the balcony. Beauti ...
From $160 per night (USD)VRBO
From $1432 per night (USD)VRBO
Blue Dolphin Oceanfront Estate, Millionaire's Row, Private Saltwater Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding ...
From $1432 per night (USD)VRBO
From $881 per night (USD)VRBO
Venetian Shores Islamorada New Home w/dock & pool
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Located in Venetian Shores, Islamorada Luxurious bayside waterfront home on a wide canal with easy access to the ocean ...
From $881 per night (USD)VRBO
From $354 per night (USD)VRBO
A 57-foot trawler in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in a friendly marina with a restaurants, gift shop, tiki bar, kayaks, jet skis, and charter fishing boats minute ...
From $354 per night (USD)VRBO
From $474 per night (USD)VRBO
Boat, Fish, Swim from Your Own 70' Dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come Play! Your 70-foot private dock provides instant access to fun – whether boating, fishing, swimming or relaxing und ...
From $474 per night (USD)VRBO
From $403 per night (USD)VRBO
Sea Glass Cottage Beautiful Canal Front Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sea Glass Cottage 2b 2b canal front home. Bring your boat or two, and enjoy your vacation or holiday relaxing and playi ...
From $403 per night (USD)VRBO
From $203 per night (USD)VRBO
Ocean Side Condo In Paradise Mm 76.5-Islamorada, Fl (28 day minimum required)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a quaint, ocean side condo with full amenities and easy access for fishing, diving, snorkeling and much more.The ...
From $203 per night (USD)VRBO
From $640 per night (USD)VRBO
The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital o ...
From $640 per night (USD)VRBO
From $1018 per night (USD)VRBO
Private Beachfront Paradise
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Village of Islamorada - Vacation Rental License No. 24-0248 This home is remodeled every year in some way or form...We ...
From $1018 per night (USD)VRBO
From $216 per night (USD)VRBO
October last Minute Special ...Bayside Condo with Beach, Pool, Marina & Dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
October Special 10/18 to 11/2 Your escape to our tropical paradise begins as you enter through the private gates of our ...
From $216 per night (USD)VRBO
From $1463 per night (USD)VRBO
Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
OSPREY BAY VILLA – Your private bayfront escape in the heart of Islamorada, Florida Keys! Relax and enjoy incredible p ...
From $1463 per night (USD)VRBO
From $413 per night (USD)Expedia
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
"Windley Cottage" is a private home in the exclusive gated community of Angler's Reef in Islamorada. This welcoming, ...
From $413 per night (USD)Expedia
From $239 per night (USD)VRBO
Beautiful Ocean Access Islamorada Condo. MM 76.5 Bring your Boat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Discounted 3 to 6 months rentals. Plan your perfect getaways to paradise. 1/1 Fully Renovated Beautifully Designed Condo ...
From $239 per night (USD)VRBO
From $630 per night (USD)VRBO
GREAT LOCATION !!! ** White Marlin Beach House, Islamorada FLORIDA KEYS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Contact owner for rates and availability at (305-431-2006). Relax in Islamorada, Florida Keys... 'Sport Fishing Capital ...
From $630 per night (USD)VRBO
From $830 per night (USD)VRBO
Beach Dream House, relax and enjoy the clear waters of Islamorada FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our Dream Beach House where you can enjoy the most panoramic views in Islamorada, Florida. Enjoy the sun risi ...
From $830 per night (USD)VRBO
From $152 per night (USD)VRBO
NEW-Summer Sea - Sweet updated 1B Apartment w/ Garden View Apt 125
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 bedroom apartment new to the rental market! Modern and updated, this first floor unit has a gorgeous kitchen with stai ...
From $152 per night (USD)VRBO
From $445 per night (USD)VRBO
Stunning Bayfront Townhouse with Boat Slip/ Marina Access - A Luxurious Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Our Cozy Townhouse at Futura Yacht Club! Nestled right by the ocean, our townhouse offers a peaceful escape ...
From $445 per night (USD)VRBO
From $2676 per night (USD)VRBO
Caribee Beach House ~ Private Islamorada Beach Estate W/ Heated Pool & Dockage
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Caribee Beach House! Discover the enchanting charm of Caribee Beach House, where the timeless allure of old- ...
From $2676 per night (USD)VRBO
From $330 per night (USD)VRBO
Anglers Reef Islamorada Vacation Rental 2/2.5 updated 131 Anglers Way
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Village of Islamorada license #24-0369 131 Anglers Way, Islamorada, FL This Villa has 2 bedrooms (one with king bed and ...
From $330 per night (USD)VRBO
From $630 per night (USD)VRBO
GREAT LOCATION !!! White Marlin Beach House, Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Contact owner for rates and availability (305-431-2006). Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of ...
From $630 per night (USD)VRBO