Islamorada Rentals
From $451 per night (USD)VRBO
Beautiful Harbor Front Oceanside Home on the Atlantic Ocean
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Oceanside 3/3 located on beautiful 10 acre harbor. Amazing natural surroundings, harbor & ocean views. New furnishings, ...
From $451 per night (USD)VRBO
From $1271 per night (USD)Expedia
Opulent waterfront estate with dock, pool, hot tub & rooftop view - dog-friendly
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Waterfront Wonder Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1271 per night (USD)Expedia
From $380 per night (USD)VRBO
Keys Villa - Secluded tropical paradise located on the water!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a q ...
From $380 per night (USD)VRBO
From $1051 per night (USD)Expedia
Marlin House @ Tarpon Point
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Stunning ocean views from all living levels & a waterfront pool! The Space: Welcome to the captivating Marlin ...
From $1051 per night (USD)Expedia
From $123 per night (USD)VRBO
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 $123 per night (USD)VRBO
From $289 per night (USD)Expedia
SPECTACULAR OCEANFRONT VIEWS , FREE WIFI, HD SMART TV'S, SUMMER SPECIAL RATES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OCEAN VIEWS EVERYWHERE in this Gorgeous 2 Bedroom/2bath Apartment overlooking the ATLANTIC OCEAN on next to top floor!! ...
From $289 per night (USD)Expedia
From $155 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 $155 per night (USD)VRBO
From $459 per night (USD)Expedia
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a la ...
From $459 per night (USD)Expedia
From $170 per night (USD)VRBO
STUNNING CONDO with BALCONY/POOL in Oceanfront Building in beautiful Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Gorgeous 2 bedroom 2 bath condo all on one floor with HEATED POOL, DOCK FOR FISHING, AND OUTDOOR BALCONY. Gated commun ...
From $170 per night (USD)VRBO
From $3512 per night (USD)VRBO
Tea Table Key Private Island Estate and Wedding Venue
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Tea Table Key Private Island Estate and Wedding Venue An extremely rare and stunning private island, accessible by car, ...
From $3512 per night (USD)VRBO
From $453 per night (USD)VRBO
Anglers Reef Islamorada Ocean Views DOCK Beach Pool Boat Slip NO ROAD NOISE!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
INTERIOR LOT—-NO ROAD NOISE—-BOAT SLIP AVAILABLE———Interior Painted Jan 2024---New Furniture in Family Room---Beautifull ...
From $453 per night (USD)VRBO
From $374 per night (USD)Expedia
Anglers Reef Islamorada 2/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Village of Islamorada Vacation Rental license #24-0372. 113 Anglers Way Call Jennifer for more information 305-240-0592. ...
From $374 per night (USD)Expedia
From $396 per night (USD)VRBO
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come stay at the Tipsy Turtle in Angler's Reef! This magnificent home with ocean views from all 4 balconies is located ...
From $396 per night (USD)VRBO
From $360 per night (USD)Expedia
Casa Mia 7862778706
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Absolutely comfortable keys Home , great location to restaurants and activities, two bedroom and two full bath upstairs ...
From $360 per night (USD)Expedia
From $254 per night (USD)VRBO
AQUAMARINE OCEANVIEW+””SPECIAL RATES””+\nDOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE EMAIL US WITH ANY QUESTIONS??? WE ARE HAPPY TO PROVIDE THE ANSWERS ABOUT OUR PROPERTY, OUR RESORT, RESTAURANTS, ...
From $254 per night (USD)VRBO
From $356 per night (USD)Expedia
Tropical Escape | Sea Gulls 407 ~ Weekly Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Located right on the Atlantic Ocean, in the heart of the Florida Keys on Plantation Key - the sport fishing and ...
From $356 per night (USD)Expedia
From $740 per night (USD)VRBO
Large Canal Front Family home in the heart of Islamorada
- Bedrooms:
- 3
- 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 $523 per night (USD)Expedia
Waterfront with a pool & private beach access.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront with pool. Private beach access within a mile. All amenities needed to enjoy a fun and relaxing vacation. A f ...
From $523 per night (USD)Expedia
From $497 per night (USD)VRBO
Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
LIC# 24-0055. 2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living amenities in ...
From $497 per night (USD)VRBO
From $922 per night (USD)Expedia
3 King Beds, 2 Pools, NEW~Kayaks/Bikes~EV charger
- Bedrooms:
- 3
- 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 $922 per night (USD)Expedia
From $297 per night (USD)VRBO
Sunset from our own Private Balcony Directly over the Bay
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Paradise in the Upper Keys. Just under 1 1/2 hrs. from Miami you can rent a piece of Heaven this Winter Season. Prime co ...
From $297 per night (USD)VRBO
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Beautiful oceanfront resort located at mile marker 73.8
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
We are committed to providing outstanding service and a great vacation experience to all of our guests. While Caloosa Co ...
Click For PricingExpedia
From $330 per night (USD)VRBO
Ocean Harbour P21 ~ Modern Oceanfront Islamorada Condo with Boat Slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This opulent condo is located within Ocean Harbour which is one of Islamorada’s most sought after gated communities feat ...
From $330 per night (USD)VRBO
From $222 per night (USD)Expedia
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)Expedia
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)VRBO
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)VRBO
From $1647 per night (USD)Expedia
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)Expedia
Click For PricingVRBO
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 $531 per night (USD)VRBO
Breathtaking Bay Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
76004 Overseas Highway - Enjoy spectacular sunsets while drinking an iced cold beverage on the observation deck of this ...
From $531 per night (USD)VRBO
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 $461 per night (USD)Expedia
Anglers Reef Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 Bed & 2.5 Bath Villa in Anglers Reef .Upscale gated community with resort living in the Florida Keys. Everything you n ...
From $461 per night (USD)Expedia
From $452 per night (USD)VRBO
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)VRBO
From $805 per night (USD)Expedia
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)Expedia
From $355 per night (USD)VRBO
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)VRBO
From $415 per night (USD)Expedia
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)Expedia
From $210 per night (USD)VRBO
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)VRBO
From $734 per night (USD)Expedia
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)Expedia
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
From $408 per night (USD)VRBO
Oceanside Resort... Oceanview unit with kayaks, paddleboards and walk in beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Artist's Cottage at Anglers Reef #136 - This beautiful home is located in Angler's Reef, a gated oceanfront communit ...
From $408 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 ...
Click For PricingVRBO
From $686 per night (USD)VRBO
Oceanfront, Pool, Dock... Checks all the boxes!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
141 LeSerra Lane - Freewheeler Vacations newest weekly rental is now available for your next Islamorada Vacation! Locate ...
From $686 per night (USD)VRBO
Click For PricingVRBO
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)Expedia
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)Expedia
From $1605 per night (USD)VRBO
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)VRBO
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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 ...
Click For PricingExpedia
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)Expedia
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)Expedia
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)VRBO
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)VRBO
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 $1114 per night (USD)VRBO
3 Bedroom Private Oceanfront House - Sol
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overl ...
From $1114 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 $438 per night (USD)Expedia
Unbelievable Second Floor Ocean View Studio with Gorgeous Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Experience the beauty of Islamorada in this spacious second-floor studio, thoughtfully designed to accommodate up to thr ...
From $438 per night (USD)Expedia
From $351 per night (USD)VRBO
Gorgeous Ocean Views, Ground Floor Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Unbelievable Ground Floor Ocean View Studio with Gorgeous Views! Experience the beauty of Islamorada in this spacious gr ...
From $351 per night (USD)VRBO
From $392 per night (USD)Expedia
Island Retreat Oceanview 1BR Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Embrace the tranquility of island living in this spacious second-floor ocean-view suite, designed to accommodate up to 6 ...
From $392 per night (USD)Expedia
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 $386 per night (USD)Expedia
Florida Keys Spacious 1 BR with 2 Balconies Pool view
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Immerse yourself in the serenity of island life with this spacious second-floor pool-view suite thoughtfully designed to ...
From $386 per night (USD)Expedia
From $388 per night (USD)VRBO
1BR with Den, Living Room, Kitchen: Marina and Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your island retreat! This spacious ground-floor Den Suite offers the perfect blend of relaxation and fun, com ...
From $388 per night (USD)VRBO
From $449 per night (USD)Expedia
Ground Floor 1BR with Den and Two Balconies
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
This spacious suite offers comfort and convenience and is located on the ground floor with a pool and partial ocean view ...
From $449 per night (USD)Expedia
From $414 per night (USD)VRBO
Relax and Recharge in Islamorada – Ground Floor Suite
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Start your day with coffee on your private patio, soaking in the fresh sea breeze as you plan your Florida Keys adventur ...
From $414 per night (USD)VRBO
From $419 per night (USD)Expedia
1 BR Condo Oceanfront Resort and Marina
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Immerse yourself in the tranquility of island living with this spacious first-floor pool-view suite, perfectly designed ...
From $419 per night (USD)Expedia
From $460 per night (USD)VRBO
Keys Dreams: 1 BR Condo
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Discover the spacious comfort of our 1-bedroom, 2-bathroom suite, offering a tranquil haven for guests to unwind. Relax ...
From $460 per night (USD)VRBO
From $365 per night (USD)Expedia
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)Expedia
From $226 per night (USD)VRBO
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)VRBO
From $1320 per night (USD)Expedia
3 bedroom, 3.5 bath luxurious condo 402 at Maison in Islamorada
- Bedrooms:
- 3
- 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 $1320 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
Click For PricingVRBO
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 ...
Click For PricingVRBO
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 $425 per night (USD)VRBO
Futura Yacht Club Bayfront Townhome with Endless Sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Endless Sunsets!! This is a beautiful Bayfront Townhome in Islamorada's popular Futura Yacht Club. 3 level townhome w ...
From $425 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 $562 per night (USD)VRBO
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)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