Islamorada Rentals
From $201 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 $201 per night (USD)VRBO
From $340 per night (USD)Expedia
Bayside: 1st Floor Apartment in Native Hammock on Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a nat ...
From $340 per night (USD)Expedia
From $1470 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 $1470 per night (USD)VRBO
From $842 per night (USD)Expedia
Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private 2acre Single Family Home awaits! Just another day in Paradise. Located at 75.7MM! Cozy, quiet, 3 bedroom (1 K ...
From $842 per night (USD)Expedia
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)Expedia
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)Expedia
From $420 per night (USD)VRBO
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 $420 per night (USD)VRBO
From $685 per night (USD)Expedia
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 $685 per night (USD)Expedia
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 $514 per night (USD)Expedia
Anglers Reef- Family Friendly Community at a Fraction of the Cost.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This Property is fully insured for rentals and licensed by the Village of Islamorada, license #24-0318. Welcome to 134 ...
From $514 per night (USD)Expedia
From $328 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 $328 per night (USD)VRBO
From $228 per night (USD)Expedia
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)Expedia
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 $1050 per night (USD)Expedia
Islamorada Boaters Paradise with 70' Dock and private beach access..
- Bedrooms:
- 5
- 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 $1050 per night (USD)Expedia
From $358 per night (USD)VRBO
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on ...
From $358 per night (USD)VRBO
From $175 per night (USD)Expedia
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 $175 per night (USD)Expedia
Click For PricingVRBO
Islamorada Gem
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A completely renovated oceanfront townhome in beautiful Islamorada in the Florida Keys. 3 Story spacious 2 bedroom 2. ...
Click For PricingVRBO
From $366 per night (USD)Expedia
Beautiful vacation home in the heart of Islamorada , Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A perfect Keys home located in the heart of Islamorada in the sought-after Port Antigua community with access to the hom ...
From $366 per night (USD)Expedia
From $254 per night (USD)VRBO
BOOK YOUR DREAM VACATION at BEACON REEF - Special deal 5\/11-6\/14 2025
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
SPECIAL DEAL FOR May 11-June 14 2025 ONLY!!! World Famous Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Perso ...
From $254 per night (USD)VRBO
From $176 per night (USD)Expedia
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)Expedia
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 $730 per night (USD)Expedia
3BR2.5BA OceanFRONT HOME-PanoramicOceanViews-HugeDecks-Quiet Location-Optl Slip
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
THERE ARE SOME HOMES WITH OCEAN PEEKS OR PARTIAL VIEWS THRU THE TREES, BUT FOR PANORAMIC UNOBSTRUCTED OCEAN VIEWS - FROM ...
From $730 per night (USD)Expedia
From $287 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 $287 per night (USD)VRBO
From $325 per night (USD)Expedia
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)Expedia
From $146 per night (USD)VRBO
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)VRBO
From $1306 per night (USD)Expedia
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 $1306 per night (USD)Expedia
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)Expedia
*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)Expedia
From $457 per night (USD)VRBO
132 Anglers Reef Islamorada- POOL, DOCK, BIKES INCL
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
VR License #24-4011 132 Anglers Way is an Adorable Key West style home in Anglers Reef. Small gated community located a ...
From $457 per night (USD)VRBO
From $533 per night (USD)Expedia
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 $533 per night (USD)Expedia
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 $1362 per night (USD)Expedia
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 $1362 per night (USD)Expedia
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 $158 per night (USD)Expedia
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 $158 per night (USD)Expedia
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)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 $293 per night (USD)Expedia
From $318 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 $318 per night (USD)VRBO
From $687 per night (USD)Expedia
Latitude Adjustment FLKeys
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Latitude Adjustment, Islamorada, Florida This home is our families' paradise in the Florida Keys and we want to share it ...
From $687 per night (USD)Expedia
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 $211 per night (USD)Expedia
Exec Bay w\/Heated Pool, Marina, Beach, Pets 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 $211 per night (USD)Expedia
From $428 per night (USD)VRBO
By The Sea ~ Islamorada Home with Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Canal front 2/2 with ocean views and relaxing breezes! The Space: This canal front two bedroom two bathroom ho ...
From $428 per night (USD)VRBO
From $239 per night (USD)Expedia
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 $239 per night (USD)Expedia
From $858 per night (USD)VRBO
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 $858 per night (USD)VRBO
From $1367 per night (USD)Expedia
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)Expedia
From $289 per night (USD)VRBO
Ocean View Condo is a 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 $289 per night (USD)VRBO
From $393 per night (USD)Expedia
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 $393 per night (USD)Expedia
From $410 per night (USD)VRBO
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 $410 per night (USD)VRBO
From $410 per night (USD)Expedia
Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
- VR#258 - Saturday check-in. 2 bedroom and 2.5 bath at 117 Anglers Way. Awesome family get-a-away in beautiful Islamor ...
From $410 per night (USD)Expedia
From $553 per night (USD)VRBO
Islamorada-Anglers Reef-LARGE\/updated\/Views DOCKAGE AVAILABLE
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Village of Islamorada license #24-0370 138 Anglers Way and boat slip #1 for 26' max boat length for this slip (extra fee ...
From $553 per night (USD)VRBO
From $417 per night (USD)Expedia
Paradise with surrounding beaches and amazing fishing!!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to paradise! This waterfront home is in the heart of the Florida Keys. This 3 bedroom 3 bath home comfortably sl ...
From $417 per night (USD)Expedia
From $1606 per night (USD)VRBO
A True Islamorada Oasis with Breathtaking Bay Views
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
Little Bay Compound - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a privat ...
From $1606 per night (USD)VRBO
From $571 per night (USD)Expedia
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 $571 per night (USD)Expedia
From $362 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 $362 per night (USD)VRBO
From $1190 per night (USD)Expedia
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 $1190 per night (USD)Expedia
From $220 per night (USD)VRBO
Florida Keys' Jewel - Executive Bay Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
An ample 1,400 sq ft. town home in the heart of Islamorada. Two bedrooms and one bathroom upstairs. One bedroom has two ...
From $220 per night (USD)VRBO
From $118 per night (USD)Expedia
An adorable, decorated studio apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Summer Sea #333 - An adorable, decorated studio apartment that has everything you need for your stay in the keys. Summer ...
From $118 per night (USD)Expedia
From $261 per night (USD)VRBO
Oceanfront 2 Bedroom Condo with Contemporary Flair
- 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 $261 per night (USD)VRBO
From $629 per night (USD)Expedia
Poolside Maison Matecumbe #302 - Great 3 Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Poolside Maison Matecumbe #302 - Islamorada oceanfront complex...Maison Matecumbe. The unit has one level living with th ...
From $629 per night (USD)Expedia
From $2586 per night (USD)VRBO
Key West Style Estate on Private Lush Beachfront Property
- Bedrooms:
- 6
- 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 $2586 per night (USD)VRBO
From $202 per night (USD)Expedia
Deep Water Canalfront Home W \/ Boat Ramp
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Clean & updated oceanside canalfront home. Located at desirable Lower Matecumbe in the Village of Islamorada, M.M.74.B ...
From $202 per night (USD)Expedia
From $2058 per night (USD)VRBO
Your PRIVATE OCEANFRONT ESTATE awaits! Dive into the Infinity Pool & 150' Beach
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Exquisite Oceanfront - Luxury and tranquility await you at this elegant Islamorada oceanfront estate. Drive through a ga ...
From $2058 per night (USD)VRBO
From $212 per night (USD)Expedia
Serene Sunsets from Your 2 Bedroom Villa
- Bedrooms:
- 2
- 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 $212 per night (USD)Expedia
From $473 per night (USD)VRBO
Keezy Does It - Charming Islamorada Villa in Gated Anglers Reef – Pool & Kayaks
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Keezy Does It – Anglers Reef, Islamorada BOAT SLIP AVAILABLE: May 11–18 & May 24 – June 6, 2025 Escape to paradise at K ...
From $473 per night (USD)VRBO
From $753 per night (USD)Expedia
Islamorada's Premier Waterfront Neighborhood- Venetian Shores!
- Bedrooms:
- 5
- 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 $753 per night (USD)Expedia
From $244 per night (USD)VRBO
Executive Bay Club U2 ~ 3 bed \/ 3 bath + Loft Townhouse in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Executive Bay Club ~ Islamorada’s Hidden Gem! This townhouse is located in the heart of Islamorada and offer ...
From $244 per night (USD)VRBO
From $1635 per night (USD)Expedia
Direct Ocean Front Estate, Private Beach, HUGE Salt Pool\/Hottub, Private Basin!!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Oceanfront Estate on 3.5 PRIVATE. Tropical Acres in the Heart Of Islamorada. Nothing like this rental in the Keys. Feat ...
From $1635 per night (USD)Expedia
From $202 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 $202 per night (USD)VRBO
From $364 per night (USD)Expedia
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 $364 per night (USD)Expedia
From $232 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 $232 per night (USD)VRBO
From $281 per night (USD)Expedia
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 $281 per night (USD)Expedia
From $530 per night (USD)VRBO
Luxury Islamorada Oasis: Pool, Dock, Fire Pit, King Beds & Canal Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Discover Your Slice of Islamorada Paradise! Contact Us Directly for Availability Welcome to our newly remodeled, canal ...
From $530 per night (USD)VRBO
From $354 per night (USD)Expedia
Waterfront Sunset View Aqua Villa at Conch Shell @ Mangrove Resort LLC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The Conch Shell houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $354 per night (USD)Expedia
From $581 per night (USD)VRBO
Gorgeous 3\/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Townhome with all extras. Keys style with beautiful new furnishings, newly remodeled with three bedrooms plus oversized ...
From $581 per night (USD)VRBO
From $419 per night (USD)Expedia
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 $419 per night (USD)Expedia
From $447 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 $447 per night (USD)VRBO
From $1083 per night (USD)Expedia
The Bonefish House at Tarpon Point ~ 4 Bed\/4 Bath Oceanfront Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing the "Bonefish House," at Tarpon Point! This opulent, luxury, home is equipped to accommodate eight adults w ...
From $1083 per night (USD)Expedia
From $215 per night (USD)VRBO
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Executive Bay Club Condo M-1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $215 per night (USD)VRBO
From $347 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 $347 per night (USD)Expedia
From $121 per night (USD)VRBO
Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to the "Keys Life Cottage!" This beautifully updated and spacious two bedroom, one bath home is tucked away on ...
From $121 per night (USD)VRBO
From $509 per night (USD)Expedia
Waterfront Paradise Found: Explore the Serene Beauty of Islamorada!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
179 Venetian Way - NEW POOL!!! Located in Venetian Shores, one of the premier Islamorada neighborhoods, this three-bedro ...
From $509 per night (USD)Expedia
From $1618 per night (USD)VRBO
Ocean & beachfront 4 bedroom, dockage, luxury residence, Islamorada, FL Keys
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Florida Keys Beachfront Vacations at Maison Residences Maison Residences offers world-class oceanfront residences in th ...
From $1618 per night (USD)VRBO
From $135 per night (USD)Expedia
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 $135 per night (USD)Expedia
From $303 per night (USD)VRBO
Ocean & Bay Views. Welcome To Paradise!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Sleeps 4, 1 Bedroom - King Bed, 2 Full Bathrooms, Queen Sleeper Sofa, 2 TVs, Balcony, fully stocked kitchen, towels & l ...
From $303 per night (USD)VRBO
From $683 per night (USD)Expedia
Beachy 3 Bedroom Condo with Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanview Maison Matecumbe #306 - Maison Matecumbe is an exclusive gated and private boutique townhome complex. This won ...
From $683 per night (USD)Expedia
From $427 per night (USD)VRBO
Tranquil Garden View One Bedroom Cottage with Pool and Boat Basin on a Beautiful Oceanfront Prope...
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hawksbill Cottage - The Hawksbill Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all wi ...
From $427 per night (USD)VRBO
From $787 per night (USD)Expedia
Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages al ...
From $787 per night (USD)Expedia
From $315 per night (USD)VRBO
Romantic Garden View Studio Cottage Nestled in Lush Landscaping with Pool and Dockage located on ...
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kemp Cottage - The Kemp Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their o ...
From $315 per night (USD)VRBO
From $341 per night (USD)Expedia
Cozy Treetop Studio on Oceanfront Property with Pool and Boat Basin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Treehouse Cottage - The Treehouse is the upper level of Hawksbill Each cottage has it's own personality and characterist ...
From $341 per night (USD)Expedia
From $440 per night (USD)VRBO
Bayside Retreat - Adorable 3 Bedroom Bayfront Duplex with Dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayside Retreat - Completely renovated bayfront duplex home. This bayfront home consists of three bedrooms and three bat ...
From $440 per night (USD)VRBO
From $361 per night (USD)Expedia
Ocean front paradise, 6th story balcony ocean view
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Islamorada is the fishing capital of the world, and home to the famous Islamorada sandbar. 🏖️ This condo is a 6th floor ...
From $361 per night (USD)Expedia
From $339 per night (USD)VRBO
Beachfront Islamorada Villa with Dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect Islamorada getaway awaits. Sandy Pointe Villa provides panoramic water views overlooking the Florida Bay, ...
From $339 per night (USD)VRBO
From $355 per night (USD)Expedia
Bayfront Islamorada Townhome with Dock & Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy all the wonders Sandy Pointe Townhome has to offer. With breathtaking bay views, deep water dockage and a private ...
From $355 per night (USD)Expedia
From $518 per night (USD)VRBO
Islamorada's Finest Canal Front 'One Story' Vacation Home WiFi-HDTV-NO STAIRS
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Islamorada is considered the fishing capitol of the world!You can do deep sea,offshore game and back country fishing!It ...
From $518 per night (USD)VRBO
From $505 per night (USD)Expedia
No shoes, No shirt, No problem!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
125 Porto Vista Ct - No shoes, No shirt, No problem! In this Pt Antigua Pool Home, you will need to go nowhere to have a ...
From $505 per night (USD)Expedia
From $134 per night (USD)VRBO
Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautiful modern Studio apartment has just been completely remodeled and new to the rental market. Every detail has ...
From $134 per night (USD)VRBO
From $564 per night (USD)Expedia
Peaceful 2 Bedroom Oceanfront Cottage with Pool and Dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Green Cottage - The Green Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their ...
From $564 per night (USD)Expedia
From $550 per night (USD)VRBO
Charming 2 Bedroom Upstairs Home with Bay Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Little Bay Upper 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 $223 per night (USD)Expedia
Beautifully Renovated 2 Bedroom Oceanfront Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
132 Atlantic Lane - Looking for your next home away from home You cannot go wrong with this recently renovated two-bedro ...
From $223 per night (USD)Expedia
From $1032 per night (USD)VRBO
Alligator Reef Conch House, a special slice of paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Alligator Reef - Conch Home - Alligator Reef is a truly special slice of paradise with two individual homes nestled on a ...
From $1032 per night (USD)VRBO
From $328 per night (USD)Expedia
Beautiful 3 Bedroom Condo with Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ocean Harbour K-21- Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from hom ...
From $328 per night (USD)Expedia