Islamorada Rentals
From $375 per night (USD)VRBO
Tarpon Bend ocean view with boat lifts
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
3/2 Waterfront Home in Lower Matecumbe Key in Islamorada, Florida. Featuring a 70' ft private dock with 2 boatlifts (1- ...
From $375 per night (USD)VRBO
From $1079 per night (USD)Expedia
Islamorada Penthouse with Private Beach & Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: This brand new, three bedrooms, three-and-a-half-bathroom penthouse unit is located within a luxury beachfront ...
From $1079 per night (USD)Expedia
From $743 per night (USD)VRBO
Beautiful Home On The Bay
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Large Home on Florida Bay, wonderful sunsets, great fishing, diving, kayaking etc.. This home could accommodate two fam ...
From $743 per night (USD)VRBO
From $348 per night (USD)VRBO
3\/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your own tropical paradise overlooking the fabulous Florida Bay - this family favorite is just 67 miles south of Miami! ...
From $348 per night (USD)VRBO
From $383 per night (USD)VRBO
POPULAR BAYFRONT Townhouse Futura Yacht Club, Pool, Dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Your own tropical paradise in Islamorada overlooking the fabulous Florida Bay - this family favorite is just 67 miles s ...
From $383 per night (USD)VRBO
From $277 per night (USD)VRBO
RELAX in your PRIVATE Oceanfront Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Due to COVID-19 and the precedented times we are living, our home will provide hand sanitizer and have the whole house s ...
From $277 per night (USD)VRBO
From $339 per night (USD)VRBO
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 $339 per night (USD)VRBO
From $146 per night (USD)VRBO
Wake up in Paradise. Islamorada Florida - 6-month minimum without boat lift.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
(6 month minimum rental) - $4,800 per month (boat slip not included). Conveniently located on a quiet street in Port An ...
From $146 per night (USD)VRBO
From $549 per night (USD)VRBO
Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
VILLAGE. RENTAL LICENSE # VR-007 Please always send email request with dates desired , as sometimes the dates on the ca ...
From $549 per night (USD)VRBO
From $233 per night (USD)VRBO
Islamorada Paradise! Luxury Townhouse! Sleeps 4-6 Boat Slip And Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Modern Upscale duplex Home Has All The Amenities For A Wonderful And Special Vacation. King Size Master Bedroom And ...
From $233 per night (USD)VRBO
From $299 per night (USD)VRBO
Ocean Views and Secure Dockage = Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
141 Ocean Lane - "The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of thi ...
From $299 per night (USD)VRBO
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)VRBO
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)VRBO
From $150 per night (USD)VRBO
Beautiful 1 bedroom apartment, king size bed, Summer Sea Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a beautiful, recently renovated, one bedroom apartment at Summer Sea Condo. A wonderful garden view with a side ...
From $150 per night (USD)VRBO
From $545 per night (USD)VRBO
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 $545 per night (USD)VRBO
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)VRBO
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)VRBO
From $509 per night (USD)VRBO
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)VRBO
From $1804 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 $1804 per night (USD)VRBO
From $138 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 $138 per night (USD)VRBO
From $112 per night (USD)VRBO
Islamorada get-away.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cozy condo in Islamorada, mile maker 76.5. Walking or biking distance to Robbie's where you can feed the tarpons. Close ...
From $112 per night (USD)VRBO
From $166 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 $166 per night (USD)VRBO
From $650 per night (USD)VRBO
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 $650 per night (USD)VRBO
From $437 per night (USD)VRBO
Tranquil One Bedroom Cottage with Pool and Boat Basin
- 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 $437 per night (USD)VRBO
From $794 per night (USD)VRBO
Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages al ...
From $794 per night (USD)VRBO
From $315 per night (USD)VRBO
Romantic Studio Cottage Nestled in Lush Landscaping with Pool and Dockage
- 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 ...
From $315 per night (USD)VRBO
From $344 per night (USD)VRBO
Cozy Studio on Oceanfront Property with Pool
- 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 $344 per night (USD)VRBO
From $423 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 $423 per night (USD)VRBO
From $467 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 $467 per night (USD)VRBO
From $1149 per night (USD)Expedia
The Bonefish House at Tarpon Point
- 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 $1149 per night (USD)Expedia
From $281 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 $281 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 $187 per night (USD)VRBO
Executive Bay w\/Heated Pool, Beach, Dogs Allowed, 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 $187 per night (USD)VRBO
From $259 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 $259 per night (USD)VRBO
From $1777 per night (USD)VRBO
Penthouse Paradise Developer Unit with Every Upgrade Possible
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Luxurious condo located at Mile Marker 75 on the Bayside in Islamorada. Watch the stars come out as evening turns to ...
From $1777 per night (USD)VRBO
From $1471 per night (USD)VRBO
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 $1471 per night (USD)VRBO
From $172 per night (USD)VRBO
Fabulous \" Sea Breeze 41 \", 3 \/ 2 Condo located Oceanside in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience high-end coastal luxury while staying at “Sea Breeze 41” in the highly sought-after Coral Harbour Club Condom ...
From $172 per night (USD)VRBO
From $531 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 $531 per night (USD)Expedia
From $494 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 $494 per night (USD)VRBO
From $240 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 $240 per night (USD)VRBO
From $2711 per night (USD)VRBO
Modern Oceanview Paradise at Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Breathtaking 3bedroom 3bathroom oceanfront vacation home is ready to welcome your family for your next getaway. Enjoy su ...
From $2711 per night (USD)VRBO
From $821 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 $821 per night (USD)VRBO
From $1422 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 $1422 per night (USD)VRBO
From $417 per night (USD)VRBO
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)VRBO
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)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 $571 per night (USD)VRBO
From $346 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 $346 per night (USD)VRBO
From $1205 per night (USD)Expedia
The Snook House ~ 4 Bed \/ 4 Bath Luxury Oceanfront Home in Islamorada!
- 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 $1205 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)VRBO
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)VRBO
From $254 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 $254 per night (USD)VRBO
From $629 per night (USD)VRBO
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)VRBO
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 $241 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 $241 per night (USD)Expedia
From $2066 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 $2066 per night (USD)VRBO
From $209 per night (USD)VRBO
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 $209 per night (USD)VRBO
From $454 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 $454 per night (USD)VRBO
From $143 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 $143 per night (USD)Expedia
From $6431 per night (USD)VRBO
Oceanfront Oasis - Pinch me am I dreaming
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
For the ultimate Keys experience, little can compare to settling into a custom-built home boasting its own private beach ...
From $6431 per night (USD)VRBO
From $1366 per night (USD)Expedia
Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
COVID-19 Update: Sunset Reef is professionally cleaned including all linens and towels. The owners or property manager d ...
From $1366 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 $290 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 $290 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 $1362 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 $1362 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 $144 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 $144 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 $202 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 $202 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 $627 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 $627 per night (USD)VRBO
From $176 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 $176 per night (USD)VRBO
From $328 per night (USD)Expedia
Sea Gulls Oceanfront Condo 4th floor with unbelievable water views. 🏝\n
- 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)Expedia
From $334 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 $334 per night (USD)VRBO
From $2162 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 $2162 per night (USD)VRBO
From $1350 per night (USD)VRBO
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
We privately own a total of 5 boutique vacation rentals in Islamorada: VRBO listing #1576833 (5 bedroom) VRBO listing #1 ...
From $1350 per night (USD)VRBO
From $194 per night (USD)VRBO
Boating Paradise with New Pool in Islamorada!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
BAYSIDE GROUND FLOOR NO STAIRS Brand New Pool! 3 Bdrm 2 Bathroom Ground Floor Home on Deep Water Canal minutes away fro ...
From $194 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 $542 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 $542 per night (USD)VRBO
From $147 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 $147 per night (USD)VRBO
From $173 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 $173 per night (USD)VRBO
From $156 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 $156 per night (USD)VRBO
From $546 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 $546 per night (USD)Expedia
From $259 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 $259 per night (USD)VRBO
From $1703 per night (USD)VRBO
Southern Diversion Estate Islamorada low rates Nov
- 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 $1703 per night (USD)VRBO
From $481 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 $481 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 $272 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 $272 per night (USD)VRBO
From $915 per night (USD)VRBO
Beautiful Islamorada Vacation rental pool home with private beach!!!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Beautiful 5 bedroom, 3 bath pool home with 70 foot of dockage at mile marker 74.5 on the bay side. The first floor is a ...
From $915 per night (USD)VRBO
From $639 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 $639 per night (USD)VRBO
From $379 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 $379 per night (USD)VRBO
From $540 per night (USD)VRBO
Stunning 3 Bedroom Condo with Oceanviews Located in Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Bay Harbour D-114 - Beautiful modern luxury unit with three bedrooms and two full bathrooms, along with a half guest-bat ...
From $540 per night (USD)VRBO
From $1584 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 $1584 per night (USD)Expedia
From $1091 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 $1091 per night (USD)VRBO
From $589 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 $589 per night (USD)VRBO
From $964 per night (USD)VRBO
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 $964 per night (USD)VRBO
From $523 per night (USD)VRBO
Relax in Islamorada-Canal Front 3 Bedroom \/ 2 Bath Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax in Islamorada Canal Front 3 Bedroom/2 Bath Home Spacious Keys style 3 bedroom / 2 bath home located on deep cana ...
From $523 per night (USD)VRBO
From $301 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 $301 per night (USD)VRBO
From $384 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 $384 per night (USD)VRBO