Islamorada Rentals
From $458 per night (USD)VRBO
Hidden Gem Islamorada | 1st Floor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: This newly renovated unit is truly is a Hidden Gem in the heart of Islamorada! This duplex is nestled in the t ...
From $458 per night (USD)VRBO
From $452 per night (USD)Expedia
Hidden Gem Islamorada | 2nd Floor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: This newly renovated unit is truly is a Hidden Gem in the heart of Islamorada! This duplex is nestled in the t ...
From $452 per night (USD)Expedia
From $247 per night (USD)VRBO
Bayside Waterfront Home with 40 ft Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
28-day minimum rental Welcome to our paradise vacation home, away from home. This Florida Keys house has 3 bedrooms, 2. ...
From $247 per night (USD)VRBO
From $872 per night (USD)Expedia
Paradise in Venetian Shores Pool \/ SPA - Heater \/ Chiller & Commercial Ice Maker
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in prestigious Venetian Shores Islamorada's premier waterfront community! This home was completely remodeled... ...
From $872 per night (USD)Expedia
From $1367 per night (USD)VRBO
Private beach and dazzling bayside sunsets await you!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The home is located at mile marker 88.9 bayside in Islamorada. It's one of eight houses located on a mile long private ...
From $1367 per night (USD)VRBO
From $177 per night (USD)VRBO
Sunsets at Islamorada, Florida Keys. 2\/2 Townho
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Completely renovated with Mom' touch, 2 story with spiral staircase bayside townhome at Executive Bay Club. Mile Marker ...
From $177 per night (USD)VRBO
From $207 per night (USD)VRBO
Disc Apr-Jun2025 -Exec Bay w\/Heated Pool, Marina, Beach, Dogs ok, Tennis\/Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Disc Apr-Jun2025 due to pool renovation Come and relax at our beautiful Executive Bay Club (EBC) townhouse T2 in the “T ...
From $207 per night (USD)VRBO
From $332 per night (USD)Expedia
Sea Gulls Oceanfront Condo with large heated oceanfront pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About an hour and fifteen minute drive from Miami International Airport and about 90 minutes from Ft. Lauderdale to wil ...
From $332 per night (USD)Expedia
From $228 per night (USD)VRBO
Islamorada Haven on the water
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Completely remodeled one bedroom one bath unit in the fishing capital of the world, Islamorada Florida. Everything brand ...
From $228 per night (USD)VRBO
From $2242 per night (USD)VRBO
Brand New Unique Deep Water Gulf Front Estate. Beach, Pool, Hot tub and docks
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
This is a brand new house. Just completed August 2014 This unique Gulf Front property is located among Gumbo Limbo, M ...
From $2242 per night (USD)VRBO
From $325 per night (USD)VRBO
Paradise in Islamorada on the Water
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Pack your fishing rods and come to our beautiful Islamorada retreat in the fishing capitol of the world. We offer you th ...
From $325 per night (USD)VRBO
From $146 per night (USD)Expedia
IMMACULATE ONE BEDROOM CONDO WITH OCEAN VIEWS
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come unwind at our newly renovated oceanfront condo in Islamorada. Enjoy breathtaking sunrises and sunsets, or scan the ...
From $146 per night (USD)Expedia
From $1407 per night (USD)VRBO
Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Sunset Reef is professionally cleaned including all linens and towels. The owners or property manager do not do the clea ...
From $1407 per night (USD)VRBO
From $253 per night (USD)VRBO
Beautiful 2\/2 Islamorada Home Directly on Florida Bay (28 Day Minimum Rental)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our home is in Islamorada, in the middle Florida Keys. To be more specific, we are on Lower Matecumbe Key, which is the ...
From $253 per night (USD)VRBO
From $342 per night (USD)VRBO
*WINTER SPECIAL* 2 BR Waterfront Pool Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
“A Little Slice of Heaven”- completely renovated and updated in December 2020 waterfront pool home in paradise. This is ...
From $342 per night (USD)VRBO
From $176 per night (USD)VRBO
Waterfront Paradise with Free Dockage - Contact us to price your stay!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of ...
From $176 per night (USD)VRBO
From $595 per night (USD)VRBO
Elegant Bay Harbor Condo with 50 Foot Boat Slip, Heated Pool, Hot Tub, and Gym
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedr ...
From $595 per night (USD)VRBO
From $181 per night (USD)VRBO
Endless Paradise at Executive Bay Club in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
* Beautiful 3/2 townhome with tile and wood floors, close to pool and beach * 50' LCD TV with stereo system, DVD ...
From $181 per night (USD)VRBO
From $526 per night (USD)VRBO
Adorable canal front Pool Home in Plantation Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
118 Plantation Avenue - Great pool home in Islamorada, located on a deep-water canal this three-bedroom two bath home ha ...
From $526 per night (USD)VRBO
From $550 per night (USD)VRBO
Charming 2 Bedroom Ground Level Home with Bay Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Little Bay Lower Level - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a pri ...
From $550 per night (USD)VRBO
From $1409 per night (USD)VRBO
All the feels... tranquility and relaxation
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
75731 Overseas Highway - You are overcome with tranquility and relaxation as you pass through the gates of this oceanfro ...
From $1409 per night (USD)VRBO
From $234 per night (USD)VRBO
Wonderful 2 Bedroom Condo with Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Seagull's #406 - OFF-SEASON SPECIAL~ $2,500/month (plus taxes and fees) if you stay with us from now until November 15 ...
From $234 per night (USD)VRBO
From $161 per night (USD)VRBO
Beautiful 1 bedroom apartment with a Phenomenal direct bay view 312
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This apartment has a million dollar view, the kind you have always dreamed of for a vacation of a lifetime! The apartmen ...
From $161 per night (USD)VRBO
From $771 per night (USD)VRBO
Islamorada Island Getaway
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Relax and enjoy the Florida Keys lifestyle and outdoor living with full wrap around terraces. PLEASE NOTE: 28 night min ...
From $771 per night (USD)VRBO
From $293 per night (USD)VRBO
Coral Cove Resort - ‘A Fisherman’s Dream’
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy camaraderie with family and friends in this well-appointed, three-bedroom, ranch-style house in a lovely, private, ...
From $293 per night (USD)VRBO
From $319 per night (USD)VRBO
Islamorada cottage on deep water canal
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our cottage is set in a quiet neighborhood on a deep, clear, wide canal. Situated bayside at mile marker 89, there is a ...
From $319 per night (USD)VRBO
From $1350 per night (USD)VRBO
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Deep water dockage & heated pool! Modern, clean & fresh interiors make this rental perfect. Manatees visit the dock ...
From $1350 per night (USD)VRBO
From $427 per night (USD)VRBO
BRAND NEW Island-design home located in Islamorada fishing capital of the world!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
The Pink Sands House is located in the beautiful Lower Matecumbe island in close proximity to all your Class-A shopping, ...
From $427 per night (USD)VRBO
From $460 per night (USD)VRBO
Stunning 3 Bedroom Bayfront Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
194 Airstream Lane - The most spectacular bay views from this stunning Islamorada home. This newly remodeled home offers ...
From $460 per night (USD)VRBO
From $448 per night (USD)Expedia
Paradise @ Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sleeps 8, 2 Story Townhome On The Bayside, Mile Marker 87 Our Islamorada beach modern decorated townhome is waiting for ...
From $448 per night (USD)Expedia
From $695 per night (USD)VRBO
Luxurious 4-Bedroom Home with Private Pool and Beach Access in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to paradise and experience the ultimate vacation getaway at our stunning 4-bedroom, 3-bathroom canal home in the ...
From $695 per night (USD)VRBO
From $445 per night (USD)VRBO
Bay Views from this Charming 2 Bedroom Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Futura Townhome #708 - Enjoy the spectacular view of the Florida Bay from either one of two balconies in this 2-story to ...
From $445 per night (USD)VRBO
From $249 per night (USD)VRBO
A little Piece of Heaven to wash your worries away
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A fully furnished two bedroom, two bath townhouse located in Islamorada, also known as the "Fishing Capital of the World ...
From $249 per night (USD)VRBO
From $566 per night (USD)VRBO
Beautiful Pool Home with Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Safety Harbour Canalfront - SEPTEMBER SPECIAL $9750. Safety Harbour Canalfront Home. Fabulous, protected dockage right o ...
From $566 per night (USD)VRBO
From $161 per night (USD)VRBO
Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Premier 1 bedroom unit with both that stunning bay view and a view of the pool off the balcony. Fully updated with the o ...
From $161 per night (USD)VRBO
From $178 per night (USD)VRBO
New- Stunning 1 B apartment with incredible view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful apartment is new to the rental market and recently fully remodeled. Modern, clean with a stunning direct ...
From $178 per night (USD)VRBO
From $200 per night (USD)VRBO
New -Beautiful modern 1 bedroom with peek-a-boo water view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Quiet and serene, this beautiful one bedroom apartment is fully updated with all the comforts of home. Open concept kitc ...
From $200 per night (USD)VRBO
From $538 per night (USD)Expedia
WOW!! WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CLEAN-CONTACT OWNER
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
***Contact owner with description of group. *** Reach out to owner (from the contact owner section), to quickly get the ...
From $538 per night (USD)Expedia
From $237 per night (USD)VRBO
Recently Renovated Luxury Townhome in Islamorada, Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Recently renovated! A beautiful 2 bedroom 2 full bath plus loft townhome located in Executive BayClub MM87, it is a priv ...
From $237 per night (USD)VRBO
From $2097 per night (USD)VRBO
Southern Diversion Estate Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the ...
From $2097 per night (USD)VRBO
From $210 per night (USD)VRBO
A Great Place! Spacious 2\/2 retreat with ocean views in the heart of the Keys.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coral Harbor is the best kept secret in Islamorada. Quiet, gated community with ocean views, clubhouse, pool and a salt ...
From $210 per night (USD)VRBO
From $253 per night (USD)VRBO
Beautiful Cottage in Islamorada on canal front! Wifi, Smart TVs and No Stairs!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully renovated and decorated CBS home on bay side with charming details throughout. Wifi, smart TV and no stairs! ...
From $253 per night (USD)VRBO
From $515 per night (USD)VRBO
Brand New \/ Totally Renovated Luxurious Home with POOL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***POOL Built in July 2019; Tropical landscaping installed 2020/2021 with great privacy*** Located in Islamorada the pr ...
From $515 per night (USD)VRBO
From $773 per night (USD)VRBO
Charming Beach Front Home in Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
113 Sunset Drive - Come and stay in this adorable "beachy backyard" home located on the crystal-clear Atlantic Ocean! Th ...
From $773 per night (USD)VRBO
From $626 per night (USD)VRBO
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
COVID-19 Update: Sunrise Haven is professionally cleaned including all linens and towels. The owners or property manag ...
From $626 per night (USD)VRBO
From $531 per night (USD)Expedia
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
WATER FRONT CANAL HOME. BRING YOUR BOAT, LOTS OF PROTECTED DOCKAGE. FULLY UPDATED HOME. All Systems, fully functional, ...
From $531 per night (USD)Expedia
From $1584 per night (USD)VRBO
Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
TED’S PLACE License # VR052 - Minimum Stay 1 Week, Saturday thru Saturday – Unbeatable Location - 1.5 acres – Bayfront ...
From $1584 per night (USD)VRBO
From $786 per night (USD)Expedia
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Islamorada- the Fishing Capital of the World. Oceanfront living doesn't get better than this. In the heart o ...
From $786 per night (USD)Expedia
From $401 per night (USD)VRBO
3 bed 2 bath condo at Futura Yacht Club!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Completely remodeled 3 bedroom condo. Kitchen completely redone Spring of 2021 Sleeping accommodations: king bed in mas ...
From $401 per night (USD)VRBO
From $284 per night (USD)VRBO
Work from home in this slice of Islamorada paradise!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come visit this tropical, remodeled vacation home and get a taste of all Islamorada has to offer with cozy, modern and c ...
From $284 per night (USD)VRBO
From $1449 per night (USD)VRBO
OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
82754 Overseas Highway - OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Ke ...
From $1449 per night (USD)VRBO
From $265 per night (USD)VRBO
Beautifully Renovated 2 Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Futura Yacht Club #205 - This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 ...
From $265 per night (USD)VRBO
From $1718 per night (USD)VRBO
4 bedroom, Ocean front,Top tier Condo in Islamorada, Florida Keys
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing Maison Residences Unit 204, Poolside... — UP TO 32’ BOAT SLIP MAY BE AVAILABLE, CALL FOR DETAILS — A world- ...
From $1718 per night (USD)VRBO
From $254 per night (USD)VRBO
Florida Keys Plantation Key Colony on Canal with Boat lift, 7K month + Taxes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Canal side Retreat in the Colony 28 day minimum no pets! You won't believe your eyes! It looks like a cozy conch cottag ...
From $254 per night (USD)VRBO
From $483 per night (USD)VRBO
Ocean Views for DAYS!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
132 Columbus Drive - Beautifully renovated home sits right on the ocean. With panoramic ocean views from every room in t ...
From $483 per night (USD)VRBO
From $3109 per night (USD)Expedia
9 bedrooms, Heated\/Chilled Pool, Open Water Views, Boat Dockage, Sleeps 24
- Bedrooms:
- 3
- Bathrooms:
- 9
- Sleeps:
- 10
This owner operated property is the vacation spot for you and your Family. Located on Grassy Key just one hour from the ...
From $3109 per night (USD)Expedia
From $656 per night (USD)VRBO
COASTAL ELEGANCE FOR RENT IN ISLAMORADA !!! PARADISE FOUND ON DEEP WATER
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This designer REMODELED IN JULY 2021 3bdr, 2bath home is located on a 60 foot deep water dock in quiet Plantation Key, F ...
From $656 per night (USD)VRBO
From $1090 per night (USD)Expedia
Sanctuary In Paradise Featured On H G T V
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Open Ocean on “Millionaire’s Row” Unique property featuring separate: ~1BR 1BA Upstairs Suite ~2BR 2BA Downstairs Apt. ...
From $1090 per night (USD)Expedia
From $295 per night (USD)VRBO
WATERFRONT FISHING COTTAGE\/ DOCKAGE + Walking distance to world famous Lorelei
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
1940s Old Keys Fishing Cottage with dockage available. Large Waterfront property and walking distance to world famous L ...
From $295 per night (USD)VRBO
From $531 per night (USD)VRBO
Venetian Shores Pool Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Desirable Venetian Shores neighborhood. Newly renovated home with open concept kitchen, dining and living room. Convenie ...
From $531 per night (USD)VRBO
From $217 per night (USD)VRBO
Executive Bay Club Condo (2 bds + loft & 3 full baths)
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Come stay and watch the sunsets at our beautifully updated Keys townhouse at Executive Bay Club located in Islamorada on ...
From $217 per night (USD)VRBO
From $547 per night (USD)VRBO
San Remo Canal Front
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
San Remo Canalfront - Venetian Shores five bedroom and four bath home with 70 ft. dock just minutes to Snake Creek for i ...
From $547 per night (USD)VRBO
From $676 per night (USD)VRBO
THE premier gated oceanfront complex in the heart of Islamorada.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
May and June 2024 Special $3400 weekly!!....Oceanfront Maison Matecumbe #303 - Maison Matecumbe is a premier gated ocean ...
From $676 per night (USD)VRBO
From $646 per night (USD)VRBO
Paradise Found - Three Story Beach House w\/ private beach, dock and Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 Day Minimum Stay. Please contact us for specific dates of availability. 3 story bayside home with its own beach. G ...
From $646 per night (USD)VRBO
From $266 per night (USD)VRBO
Discover the Charm of Island Living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf o ...
From $266 per night (USD)VRBO
From $177 per night (USD)VRBO
Pineapple Point pet friendly paradise Islamorada\n\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Pineapple Point, where the quiet peaceful setting will entice you to relax and enjoy Keys living. Our 2 bedro ...
From $177 per night (USD)VRBO
From $362 per night (USD)VRBO
Islamorada 3\/2 condo. Futura Yacht Club Dockage, swimming pool, sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your own tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada. Futura Yacht Club is a 70 unit c ...
From $362 per night (USD)VRBO
From $370 per night (USD)VRBO
Just a Few Friends - Ocean View and Bring your Boat!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Experience all the Florida Keys has to offer in this stunning 2 bed/ 2 ½ bath condominium with an Ocean View, located in ...
From $370 per night (USD)VRBO
From $622 per night (USD)VRBO
Waterfront Oasis 2Mins2BeachTons dockage VERY Private Immediate ocean\/bay access
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Spacious five bedroom home on huge canal. Commercial Ice Machine, bait freezer, and fish cleaning station!! SUPER PRIV ...
From $622 per night (USD)VRBO
From $1056 per night (USD)Expedia
BAYSIDE PARADISE ~ Heart of Islamorada ~ Private Boat Dockage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into ou ...
From $1056 per night (USD)Expedia
From $205 per night (USD)VRBO
Indian Mound - Islamorada Keys Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Indian Mound is the ultimate family getaway! Relax in this three bedroom / two bathroom home that has recently been fur ...
From $205 per night (USD)VRBO
From $503 per night (USD)VRBO
Keys Paradise with Private Beach and Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
NOTE: --PLEASE SEND AN INQUIRY TO BE SURE YOUR DATES ARE AVAILABLE. --DOCKAGE AVAILABLE AT FOUNDERS PARK MARINA RIGHT N ...
From $503 per night (USD)VRBO
From $815 per night (USD)VRBO
Beautiful Bayfront Home with Amazing Sunsets
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This Property has a large kitchen and living area open to amazing views of the bay with 4 bedrooms and 3 full baths. Yo ...
From $815 per night (USD)VRBO
From $685 per night (USD)VRBO
Private Pool, Completely Renovated Lovely Cottage Home in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 4 bedroom, 3 bathroom pool home in lovely White Marlin beach, Islamorada, FL. Home has been completely renova ...
From $685 per night (USD)VRBO
From $288 per night (USD)VRBO
OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Centrally located at MM 75.5 in beautiful Islamorad, you are only minutes from boat ramps , great restaurants, beaches ...
From $288 per night (USD)VRBO
From $401 per night (USD)VRBO
Beautiful 'Keysey' Condo in Bay Harbour Gated Community 24-0169
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Enjoy the spirit of the Florida Keys in this 'keysey' furnished condo with everything provided. All you have to do is s ...
From $401 per night (USD)VRBO
From $410 per night (USD)VRBO
Islamorada Luxury Waterfront Condo with Boat Slip
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in ...
From $410 per night (USD)VRBO
From $378 per night (USD)VRBO
Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much mor ...
From $378 per night (USD)VRBO
From $477 per night (USD)VRBO
Unique 2 Bedroom Bay Front Home with Roof Top Terrace
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
75130 Overseas Highway - Great house in Lower Matecumbe (south side of Islamorada) at the 75-mile marker on the bayside. ...
From $477 per night (USD)VRBO
From $276 per night (USD)Expedia
Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Time to change your latitude, attitude and immerse your body and mind in the calming, soothing waters that surround our ...
From $276 per night (USD)Expedia
From $1084 per night (USD)VRBO
Canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Location, location, location! A tropical palmy dream and playground for ocean lovers. Minutes on boat from the best san ...
From $1084 per night (USD)VRBO
From $743 per night (USD)Expedia
Beautiful New Island Home for 2 Small Families
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Plan your vacation getaway in paradise at this amazing new canal-front home with all the comforts of home in a quiet nei ...
From $743 per night (USD)Expedia
From $295 per night (USD)VRBO
Tropical Paradise at Futura Yacht Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Futura Yacht Club is a private 70 unit community with a 53 slip marina. Easy access to the ocean through Snake Creek or ...
From $295 per night (USD)VRBO
From $566 per night (USD)VRBO
Beautiful 3 Bedroom Condo with Ocean Views Located in Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Harbour C-312 - Beautiful three bedroom two and a half bath luxury condo at mile maker 74.5. Complex comes complete ...
From $566 per night (USD)VRBO
From $629 per night (USD)VRBO
☀️Luxury 3 BR Remodeled! Ocean View PoolSpa, MarinaBikes Boat Slip Tennis\/Pickle
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Boat Slip is available for a small weekly fee of $150 Come enjoy relaxing or being active at luxurious Bay Harbour - a ...
From $629 per night (USD)VRBO
From $278 per night (USD)VRBO
Canal front Oasis with Pool and Tiki Hut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
128 Tequesta Street - The perfect vacation home! This charming three-bedroom two bath home has everything you need for t ...
From $278 per night (USD)VRBO
From $1246 per night (USD)VRBO
Seaside Sanctuary 5 bed, 5 bath pool home
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
This impressive home is located in Islamorada on a private lagoon with quick direct access to the Florida Bay. Featurin ...
From $1246 per night (USD)VRBO
From $624 per night (USD)VRBO
Cute Canal front Venetian Shores Weekly Rental!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
107 San Remo Drive - Comfortable Venetian Shores canal home that has two-bedroom one bath upstairs and a one bedroom one ...
From $624 per night (USD)VRBO
From $239 per night (USD)VRBO
Bay Views from this Charming 3 Bedroom Canal Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
186 Airstream Lane - Located on a quiet street in Islamorada, this home offers you the best of both worlds. Fantastic, p ...
From $239 per night (USD)VRBO
From $548 per night (USD)VRBO
Panoramic Ocean Views from this 3 Bedroom Islamorada Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
137 LeSerra Lane - Beautiful designer appointed Oceanside canal home located at the mile marker 76.5 in Lower Matecumbe ...
From $548 per night (USD)VRBO
From $338 per night (USD)VRBO
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 $338 per night (USD)VRBO
From $323 per night (USD)Expedia
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 $323 per night (USD)Expedia
From $408 per night (USD)VRBO
Island Retreat Oceanview 1BR Suite
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Embrace the tranquility of island living in this spacious second-floor ocean-view suite, designed to accommodate up to 6 ...
From $408 per night (USD)VRBO
From $360 per night (USD)Expedia
Large Screened Porch, Professional Cleaning, Wifi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Oceanfront 90 mm Plantation Key , full screened in terrace 6.5 ft by 28.5 ft. Newly decorated white tile & Berber carp ...
From $360 per night (USD)Expedia
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FLORIDA KEYS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
ONLY WEEK AVAILABLE: OCTOBER 5-12, 2024. Caloosa Cove Resort and Marina is located on 10 tropical acres in Islamorada, F ...
Click For PricingVRBO
From $448 per night (USD)Expedia
Keys Villa--Islamorada private beach!
- 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 $448 per night (USD)Expedia
From $258 per night (USD)VRBO
Stunning Penthouse 3 bedroom Apartment, New
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Stunning 3 bedroom Penthouse is absolutely stunning! The photos do not due justice to the amazing ceiling, Livingro ...
From $258 per night (USD)VRBO
From $254 per night (USD)Expedia
Best location in downtown Islamorada. Beach access and boat trailer parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Unbelievable location in Islamorada Florida Keys! You have beach access and boat trailer parking. Close enough to walk a ...
From $254 per night (USD)Expedia
From $437 per night (USD)VRBO
Fantastic Bayside Townhouse
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Fantastic gated Bayside townhouse with all the bells and whistles. Excellant location with everything you need to have a ...
From $437 per night (USD)VRBO
From $267 per night (USD)Expedia
Best Location in Islamorada!! Beach access - Boat trailer parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Gorgeous and highly appointed luxury Island villa with beach access. You are right in the middle of it all with this per ...
From $267 per night (USD)Expedia