Islamorada Rentals
From $254 per night (USD)VRBO
Waterfront Islamorada Condo – Heated Pool, Marina & Deeded Boat Slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the Florida Keys from this bright 2-bedroom, 2-bath condo at Futura Yacht Club, a gated waterfront community i ...
From $254 per night (USD)VRBO
From $312 per night (USD)VRBO
Charming 3-Bed, 2-Bath Canal Home in Tavernier, FL, with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to 128 Tequesta Street, a charming three-bedroom, two-bath waterfront home designed for the perfect Florida Keys ...
From $312 per night (USD)VRBO
From $1214 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 $1214 per night (USD)VRBO
From $338 per night (USD)VRBO
Experience the relaxing vibe at Heavens Reel, a spacious 3-bedroom canal home in Tavernier.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Adorable waterfront pool home in Tavernier! Great dockage close to Tavernier Creek for easy bay and ocean access. Cozy c ...
From $338 per night (USD)VRBO
From $509 per night (USD)VRBO
Paradise Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful tranquil private beach is just the beginning of what awaits you in our completely renovated beach house. Port ...
From $509 per night (USD)VRBO
From $608 per night (USD)VRBO
Charming 3BR canal home in Islamorada, perfect for your tropical getaway!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the highly desirable Venetian Shores neighborhood, this canal-front home offers quick access to both the Ocea ...
From $608 per night (USD)VRBO
From $337 per night (USD)VRBO
Charming 3BR canal home in Tavernier, perfect for up to 6 guests!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located on a quiet street in Islamorada, this home offers you the best of both worlds. Fantastic, protected canal dockag ...
From $337 per night (USD)VRBO
From $532 per night (USD)VRBO
Enjoy a serene stay at 137 LeSerra Lane, a 3-bedroom canal retreat in Islamorada.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful designer-appointed oceanside canal home located at Mile Marker 76.5 on Lower Matecumbe Key in Islamorada. Situ ...
From $532 per night (USD)VRBO
From $378 per night (USD)VRBO
Home in Islamorada Florida
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Water Front modern home perfectly situated on the Bay side. Located on a deep-water canal that offers all sorts of enjoy ...
From $378 per night (USD)VRBO
From $772 per night (USD)Expedia
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We are proud to announce- Castaway Island has been named for KW people’s choice awards as a FINALIST for Best Vacation ...
From $772 per night (USD)Expedia
From $258 per night (USD)VRBO
Amazing Sandy Beach Sunsets + New Pool + Best Location w/ Park - Bikes & Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Come and stay in our 3 1/2 bedroom getaway by the scenic bay in breathtaking Islamorada. * Enjoy your community's privat ...
From $258 per night (USD)VRBO
From $1022 per night (USD)VRBO
Renovated Islamorada lush canal home with 2nd fl pool, ocean views and boat dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Location, location, location! A tropical paradise and playground for ocean lovers. Minutes by boat from Islamorada’s be ...
From $1022 per night (USD)VRBO
From $213 per night (USD)VRBO
Work remote, or not at all, in paradise at this cozy, beachy condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Flexible cancellation policy. Futura Yacht Club is an exclusive private, gated resort community. Not like a hotel, FYC ...
From $213 per night (USD)VRBO
From $385 per night (USD)VRBO
Beautiful 'Keysey' Condo in Bay Harbour Gated Community 26-0169
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the essence of the Florida Keys in this ‘keysey’ furnished condo, complete with all the amenities you need. S ...
From $385 per night (USD)VRBO
From $406 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 $406 per night (USD)VRBO
From $508 per night (USD)VRBO
Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much mor ...
From $508 per night (USD)VRBO
From $276 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 $276 per night (USD)VRBO
From $458 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 $458 per night (USD)VRBO
From $770 per night (USD)VRBO
Beautiful Bayfront Home with Amazing Sunsets
- Bedrooms:
- 2
- 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 $770 per night (USD)VRBO
From $589 per night (USD)VRBO
Beautiful 4/3, pool home in lovely White Marlin beach, Islamorada, FL
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 4 bedroom, 3 bathroom pool home in lovely White Marlin beach, Islamorada, FL. Serene and spacious outdoor are ...
From $589 per night (USD)VRBO
From $272 per night (USD)VRBO
OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Centrally located at MM 75.5 in beautiful Islamorad, you are only minutes from boat ramps , great restaurants, beaches ...
From $272 per night (USD)VRBO
From $2364 per night (USD)VRBO
Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Enjoy all the beauty of Islamorada's clear blue waters from your private beachfront estate. Turtle Nest Estate features ...
From $2364 per night (USD)VRBO
From $2294 per night (USD)VRBO
Charming Ocean Front Pool Home with dockage & pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Step out the door to your private oceanfront beach with pool and dock at Midnight Runner. The property features two livi ...
From $2294 per night (USD)VRBO
From $379 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 $379 per night (USD)VRBO
From $388 per night (USD)VRBO
Just a Few Friends - Ocean View and Bring your Boat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your slice of the Florida Keys at the Bay Harbour Condominium Complex in Islamorada. This bright and spacious ...
From $388 per night (USD)VRBO
From $763 per night (USD)VRBO
Waterfront Oasis 2Mins2BeachTons dockage VERY Private Immediate ocean/bay access
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Islamorada Vacation Rental LICENSE #: 26-1243 Spacious five bedroom home on huge canal. Tons of dockage, bait freezer, ...
From $763 per night (USD)VRBO
From $198 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 $198 per night (USD)VRBO
From $479 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 $479 per night (USD)VRBO
From $143 per night (USD)VRBO
Beautifully Updated Studio Apartment, Summer Sea Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautifully updated apartment is new to the rental market. Modern and clean with all the comforts of home, tropical ...
From $143 per night (USD)VRBO
From $566 per night (USD)VRBO
Spacious 5BR San Remo Canalfront iwith hot tub in Islamorada, perfect for 10 guests.
- 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 $566 per night (USD)VRBO
From $726 per night (USD)VRBO
Experience paradise at Oceanfront Maison Matecumbe 303 in beautiful Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
.Oceanfront Maison #303 - Maison is a premier gated oceanfront complex in the heart of Islamorada. This prime oceanfront ...
From $726 per night (USD)VRBO
From $627 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 $627 per night (USD)VRBO
From $867 per night (USD)VRBO
Waterfront home in the heart of the fishing capital of the world.
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 14
Forget your worries in this private water front home. This private two family home is ideal of large fishing groups and ...
From $867 per night (USD)VRBO
From $254 per night (USD)VRBO
Charming 2-bedroom condo in Islamorada with pool access and ocean views.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Futura Yacht Club #205 - This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 ...
From $254 per night (USD)VRBO
From $743 per night (USD)VRBO
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Haven is professionally cleaned including all linens and towels. The owners or property manager do not do the c ...
From $743 per night (USD)VRBO
From $253 per night (USD)Expedia
Spring & summer dates available licensed rental vr #25-0235 NO BOATS
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This is a legally licensed rental in the Village of Islamorada license # vr 131 The entire condo has been updated ...
From $253 per night (USD)Expedia
From $270 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 $270 per night (USD)VRBO
From $157 per night (USD)VRBO
Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Drive down south to enjoy the tranquil and beautiful Florida Keys. Enjoy a cozy and spacious townhome in the heart of I ...
From $157 per night (USD)VRBO
From $1763 per night (USD)VRBO
5 bedrooms, Heated/Chilled Pool, Open Water Views, Boat Dockage, Sleeps 13--15,
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
This owner operated property is the vacation spot for you and your Family. Located on Grassy Key just one hour from the ...
From $1763 per night (USD)VRBO
From $358 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 $358 per night (USD)VRBO
From $1080 per night (USD)VRBO
Egret House @ Tarpon Point
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Indulge in breathtaking ocean vistas from every living level, complemented by an inviting waterfront pool! The ...
From $1080 per night (USD)VRBO
From $1494 per night (USD)Expedia
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 $1494 per night (USD)Expedia
From $893 per night (USD)VRBO
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 $893 per night (USD)VRBO
From $304 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 $304 per night (USD)VRBO
From $560 per night (USD)VRBO
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 $560 per night (USD)VRBO
From $834 per night (USD)VRBO
Stunning 4-bedroom oceanfront home in Islamorada, perfect for 8 guests.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wake up to the sound of the ocean and step right onto your own stretch of beach. True beachfront homes in the Florida Ke ...
From $834 per night (USD)VRBO
From $461 per night (USD)VRBO
CHARMING WATERFRONT OCEANSIDE CANAL HOME-LARGE PROTECTED DOCKAGE-WiFi-SMART TVs.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
WATER FRONT CANAL HOME 3 BEDROOM/ 3 BATH HOME. BRING YOUR BOAT, LOTS OF PROTECTED DOCKAGE. FULLY UPDATED HOME. HIGH S ...
From $461 per night (USD)VRBO
From $534 per night (USD)Expedia
Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy waterfront villa with heated pool and quick access to Ocean and Gulf fishing and diving. Laid back Tiki Hut great f ...
From $534 per night (USD)Expedia
From $495 per night (USD)VRBO
ISLAMORADA WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CONTACT OWNER
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***Contact owner with description of group. *** Reach out to owner (from the contact owner section), to quickly get the ...
From $495 per night (USD)VRBO
From $241 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 $241 per night (USD)VRBO
From $225 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 $225 per night (USD)VRBO
Click For PricingExpedia
Paradise in Plantation Key/Deep Water Canal House/Boat Dock/MM 89
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise in Plantation Key. If you are looking to relax and learn about “Keys Time” you are looking in the right area! ...
Click For PricingExpedia
From $246 per night (USD)VRBO
A little Piece of Heaven to wash your worries away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A fully furnished two bedroom, two bath townhouse located in Islamorada, also known as the "Fishing Capital of the World ...
From $246 per night (USD)VRBO
From $146 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 a stunning bay view and a view of the pool off the private balcony. Fully updated with ...
From $146 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 $287 per night (USD)Expedia
Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bayside is a first floor apartment overlooking the beautiful waters of Florida Bay. Bayside is located on a small resort ...
From $287 per night (USD)Expedia
From $1375 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 $1375 per night (USD)VRBO
From $444 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 $444 per night (USD)VRBO
From $516 per night (USD)VRBO
Charming 3-bedroom canal home in Islamorada with modern amenities for 6 guests.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bayview home located at the end of a canal on Airstream Lane on Plantation Key. This beautiful property offers peaceful ...
From $516 per night (USD)VRBO
From $419 per night (USD)VRBO
Paradise @ Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Sleeps 8, 2 Story Townhome On The Bayside, Mile Marker 87 Our Islamorada beach modern decorated townhome is waiting for ...
From $419 per night (USD)VRBO
From $335 per night (USD)VRBO
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 $335 per night (USD)VRBO
From $2491 per night (USD)VRBO
Unique Deep Water Gulf Front Estate. Beach, Pool, Hot tub and docks.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This unique Gulf Front property is located among Gumbo Limbo, Mahogany, Royal Ponciana and palm trees sprinkled with ot ...
From $2491 per night (USD)VRBO
From $1029 per night (USD)VRBO
Islamorada Boaters Paradise with 70' Dock and private beach access..
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Calling all boaters and anglers! You will love our home. Nestled on a canal only 3 minutes to the bay and 10 minutes to ...
From $1029 per night (USD)VRBO
From $350 per night (USD)Expedia
Keys Kottage & Bayside Villa W/ free onsite boat ramp marina & trailer parking.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on ...
From $350 per night (USD)Expedia
From $182 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 $182 per night (USD)VRBO
From $252 per night (USD)Expedia
BOOK YOUR DREAM VACATION at BEACON REEF - SPECIAL SUMMER DEAL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
August to November, take $500 off regular price! World Famous Beacon Reef Condo (a gated community) Oceanfront Islamorad ...
From $252 per night (USD)Expedia
From $183 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 $183 per night (USD)VRBO
From $622 per night (USD)VRBO
Elegant Bay Harbor Condo with 50 Foot Boat Slip, Heated Pool, Hot Tub, and Gym
- Bedrooms:
- 2
- 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 $622 per night (USD)VRBO
From $300 per night (USD)VRBO
Executive Bay Club Bayfront/Beachfront paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Watch the sunset from your private balcony from this bay front , beach front townhouse/condo. Recently remodeled and ful ...
From $300 per night (USD)VRBO
From $293 per night (USD)VRBO
Islamorada Paradise - Canal Front & Private Beach Access
- 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 $293 per night (USD)VRBO
From $1391 per night (USD)VRBO
Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Sunset Reef is professionally cleaned including all linens and towels. The owners or property manager do not do the clea ...
From $1391 per night (USD)VRBO
From $249 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 $249 per night (USD)VRBO
From $147 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 $147 per night (USD)VRBO
From $300 per night (USD)Expedia
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 $300 per night (USD)Expedia
From $334 per night (USD)VRBO
Islamorada cottage on deep water canal
- Bedrooms:
- 1
- 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 $334 per night (USD)VRBO
From $189 per night (USD)VRBO
Sunsets at Islamorada, Florida Keys. 2/2 Townhome at Executive Bay Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Conveniently located 2 story bayside townhome at Executive Bay Club. Mile Marker 87.2. - Aprox. 1300 sq. ft. - 2 bedroom ...
From $189 per night (USD)VRBO
From $382 per night (USD)VRBO
Exec Bay w/heated Pool, Marina, Beach, Pets ok, Tennis/Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come and relax at our beautiful Executive Bay Club (EBC) townhouse T2 in the “T” building. EBC is located in Islamorada, ...
From $382 per night (USD)VRBO
From $334 per night (USD)Expedia
Ocean Harbour Condominium is an Oceanfront Fisherman's Paradise in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This spacious two bedroom, two bath condominium overlooking the ocean is located on a quiet 12 acre private gated commun ...
From $334 per night (USD)Expedia
From $400 per night (USD)VRBO
Sunset Access + Boat Basin | Walkable Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Unique, thoughtfully updated retreat in the heart of Islamorada with rare access to a private boat basin and f ...
From $400 per night (USD)VRBO
From $1780 per night (USD)VRBO
Experience luxury at Little Bay Compound in Islamorada with stunning views.
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Little Bay Compound - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a privat ...
From $1780 per night (USD)VRBO
From $643 per night (USD)VRBO
Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This tropical oasis includes a heated pool and dock that reaches out onto a protected lagoon that opens into the Florida ...
From $643 per night (USD)VRBO
From $271 per night (USD)VRBO
Newly redone condo with spectacular 5th floor open bay view.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Clean contemporary condo, with very nice accommodations. 2 Bedrooms with 2 bathroom/Showers, and also murphy bed in out ...
From $271 per night (USD)VRBO
From $1222 per night (USD)VRBO
The Snook House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This impressive home is tastefully decorated and features an open floor plan, soaring ceilings, an unimpeded, nearly 180 ...
From $1222 per night (USD)VRBO
From $269 per night (USD)VRBO
Charming 2-bedroom oceanfront condo in Islamorada, ideal for a tropical getaway.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ocean Harbour K-44 - Islamorada's Desirable Ocean Harbour Condominium Complex. Remodeled two-bedroom two bath unit with ...
From $269 per night (USD)VRBO
From $2798 per night (USD)VRBO
Experience luxury in this 5-bedroom oceanfront home in Islamorada, perfect for 12 guests.
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 12
Kara Pan - Islamorada's Premier Oceanfront Estate Home... Kara Pan 1. Discreet Key West style home is situated on a four ...
From $2798 per night (USD)VRBO
From $2105 per night (USD)VRBO
Discover luxury in this 5-bedroom exquisite oceanfront pool home in beautiful Islamorada.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Exquisite Oceanfront - Luxury and tranquility await you at this elegant Islamorada oceanfront estate. Drive through a ga ...
From $2105 per night (USD)VRBO
From $227 per night (USD)VRBO
Sandy Pointe: Cozy 2BR condo in Islamorada with sandy beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Serene Sunsets from your villa! Sandy Pointe is located in prestigious Port Antigua on Lower Matecumbe. This condo is a ...
From $227 per night (USD)VRBO
From $850 per night (USD)VRBO
Experience luxury at Casa De Bliss, a spacious 4-bedroom canalfront retreat in Islamorada.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Casa De Bliss - Canal front Venetian Shores...Unwind on your trip to the Keys at Casa De Bliss. This four bedrooms, four ...
From $850 per night (USD)VRBO
From $261 per night (USD)VRBO
Executive Bay Club U2 ~ 3 bed / 3 bath + Loft Townhouse in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Executive Bay Club U2! Located in the heart of Islamorada, this fully upgraded townhouse offers everything y ...
From $261 per night (USD)VRBO
From $232 per night (USD)VRBO
Fabulous \" Sea Breeze 41 \", 3 / 2 Condo & 33' Boat Slip- Oceanside in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Luxury Island Retreat w/ Boat Slip, Pool, Marina & Private Balcony – “Sea Breeze 41” | Coral Harbour Club, Islamorada W ...
From $232 per night (USD)VRBO
From $407 per night (USD)VRBO
Key Lime Cottage in Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Relax, Recharge & Explore – Detached Islamorada Cottage w/ Pool, Paddleboards & Fire Pit ☀️ Welcome to your own private ...
From $407 per night (USD)VRBO
From $208 per night (USD)VRBO
Keys Cozy Townhouse
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy breathtaking sunset from your own private beach. Cottage nautical townhouse with your outside terrace. Best r ...
From $208 per night (USD)VRBO
From $308 per night (USD)VRBO
Islamorada Bayfront Townhouse in Executive Bay Club
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront beautiful double townhouse with stunning bay views. Watch the sunsets from your balcony or from the beach right ...
From $308 per night (USD)VRBO
From $627 per night (USD)VRBO
Luxury Islamorada Oasis: Pool, Dock, Fire Pit, King Beds & Canal Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover Your Slice of Islamorada Paradise! Contact Us Directly for Availability Welcome to our newly remodeled, canal ...
From $627 per night (USD)VRBO
From $370 per night (USD)VRBO
Sunsets on the bay at Villa Mia
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy sunsets on the bay at Villa Mia! We created a peaceful retreat for our family and friends to enjoy. It is ...
From $370 per night (USD)VRBO
From $481 per night (USD)VRBO
🌴 Casa 157 @ White Marlin Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*3 Bedrooms, 2 Baths, Single Story Charming Keys House, Washer /dryer, Wifi/cable, backyard is completely fenced in * ...
From $481 per night (USD)VRBO
From $1119 per night (USD)VRBO
The Bonefish House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the "Bonefish House" at Tarpon Point! This opulent, luxury, home is equipped to accommodate eight adults wit ...
From $1119 per night (USD)VRBO
From $344 per night (USD)Expedia
Gulf View Retreat @ Bay Harbor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: 2/2 Bay harbor condo with stunning Marina and Ocean views! The Space: Escape to the breathtaking Gulf View Ret ...
From $344 per night (USD)Expedia
From $237 per night (USD)VRBO
Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Keys Life Cottage! Experience the laid-back charm of Islamorada at Keys Life Cottage, a beautifully coastal- ...
From $237 per night (USD)VRBO
From $153 per night (USD)VRBO
Tropical Condo On The Ocean 1 BR/1 BA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Please note: We require a 28 day minimum rental. Located on the Ocean at mile marker 90 on Plantation Key, in Islamor ...
From $153 per night (USD)VRBO