Islamorada Rentals
- From $450 per night (USD)
VRBO
Islamorada's Finest Canal Front 'One Story' Vacation Home WiFi-HDTV-NO STAIRS
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Islamorada is considered the fishing capitol of the world!You can do deep sea,offshore game and back country fishing!It ...
From $450 per night (USD)VRBO
- From $432 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 $432 per night (USD)VRBO
- From $478 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 four single family homes all ...
From $478 per night (USD)VRBO
- From $448 per night (USD)
VRBO
Charming 2 Bedroom Upstairs Home with Bay Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $448 per night (USD)VRBO
- From $165 per night (USD)
VRBO
Islamorada Piece Of Paradise! Executive Bay Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come, Enjoy and Relax in our beautiful piece of PARADISE in the Florida Keys. The Executive Bay Club is located in Islam ...
From $165 per night (USD)VRBO
- From $196 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 $196 per night (USD)VRBO
- From $319 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 $319 per night (USD)VRBO
- From $100 per night (USD)
VRBO
Wake up in Paradise! Florida Keys - Islamorada (6 month minimum rental)
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
(6 month minimum rental) - $3,100 per month (without boat slip). Slip an additional $300 a month. Situated on a quiet s ...
From $100 per night (USD)VRBO
- From $394 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 $394 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Islamorada Paradise! Luxury Townhouse! Sleeps 4-6 Boat Slip And Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Modern Upscale duplex Home Has All The Amenities For A Wonderful And Special Vacation. King Size Master Bedroom And ...
From $200 per night (USD)VRBO
- From $234 per night (USD)
VRBO
Ocean Views and Secure Dockage = Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
141 Ocean Lane - "The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of thi ...
From $234 per night (USD)VRBO
- From $432 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 $432 per night (USD)VRBO
- From $1551 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 $1551 per night (USD)VRBO
- From $105 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 $105 per night (USD)VRBO
- From $100 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 $100 per night (USD)VRBO
- From $298 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 $298 per night (USD)VRBO
- From $545 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 $545 per night (USD)VRBO
- From $368 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 four single family h ...
From $368 per night (USD)VRBO
- From $627 per night (USD)
VRBO
Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of four single fami ...
From $627 per night (USD)VRBO
- From $239 per night (USD)
VRBO
Romantic Studio Cottage Nestled in Lush Landscaping with Pool and Dockage
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Kemp Cottage - The Kemp Cottage is located in Turtle Cove, Islamorada's quaint enclave of four single family homes all w ...
From $239 per night (USD)VRBO
- From $269 per night (USD)
VRBO
Cozy Studio on Oceanfront Property with Pool
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Treehouse Cottage - The Treehouse Studio is located in Turtle Cove, Islamorada's quaint enclave of four single family ho ...
From $269 per night (USD)VRBO
- From $360 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 $360 per night (USD)VRBO
- From $410 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 $410 per night (USD)VRBO
- From $840 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 $840 per night (USD)Expedia
- From $200 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 $200 per night (USD)VRBO
- From $314 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 $314 per night (USD)Expedia
- From $314 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 $314 per night (USD)VRBO
- From $223 per night (USD)
VRBO
Bayside Waterfront Home with 40 ft Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
28-day minimum rental Welcome to our paradise vacation home, away from home. This Florida Keys house has 3 bedrooms, 2. ...
From $223 per night (USD)VRBO
- From $1877 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 $1877 per night (USD)VRBO
- Click For Pricing
Expedia
Walk to the best Islamorada restaurants | Little Basin Villas | Key Lime Villa 2
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Key Lime Villa #2 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart o ...
Click For PricingExpedia
- From $675 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 $675 per night (USD)VRBO
- From $921 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 $921 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Beautiful Venetian Shores Waterfront 4 bedroom Home away from Home!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This charming home sits on a large tropical lot (100' dock) with a great tiki and a large hot tub for late afternoon rel ...
From $500 per night (USD)VRBO
- From $150 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 $150 per night (USD)VRBO
- From $172 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 $172 per night (USD)VRBO
- From $172 per night (USD)
Expedia
IMMACULATE ONE BEDROOM CONDO WITH OCEAN VIEWS
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come unwind at our newly renovated oceanfront condo in Islamorada. Enjoy breathtaking sunrises and sunsets, or scan the ...
From $172 per night (USD)Expedia
- From $3816 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 $3816 per night (USD)VRBO
- From $1204 per night (USD)
Expedia
Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
COVID-19 Update: Sunset Reef is professionally cleaned including all linens and towels. The owners or property manager d ...
From $1204 per night (USD)Expedia
- From $225 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 $225 per night (USD)VRBO
- From $250 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 $250 per night (USD)VRBO
- From $315 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 $315 per night (USD)VRBO
- From $1344 per night (USD)
VRBO
A True Islamorada Oasis with Breathtaking Bay Views
- Bedrooms:
- 6
- Bathrooms:
- 5
- 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 $1344 per night (USD)VRBO
- From $425 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 $425 per night (USD)VRBO
- From $241 per night (USD)
VRBO
Newly redone condo with spectacular 5th floor open bay view.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Clean and newly refurbished condo, with very nice accommodations. 2 Bedrooms with 2 bathroom/Showers, and also murphy be ...
From $241 per night (USD)VRBO
- From $1000 per night (USD)
VRBO
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 $1000 per night (USD)VRBO
- From $190 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 $190 per night (USD)VRBO
- From $90 per night (USD)
VRBO
An adorable, decorated studio apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summer Sea #333 - An adorable, decorated studio apartment that has everything you need for your stay in the keys. Summer ...
From $90 per night (USD)VRBO
- From $209 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 $209 per night (USD)VRBO
- From $508 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 $508 per night (USD)VRBO
- From $2165 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 $2165 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Deep Water Canalfront Home W \/ Boat Ramp
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Clean & updated oceanside canalfront home. Located at desirable Lower Matecumbe in the Village of Islamorada, M.M.74.B ...
From $180 per night (USD)VRBO
- From $1695 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 $1695 per night (USD)VRBO
- From $179 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 $179 per night (USD)VRBO
- From $413 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 $413 per night (USD)VRBO
- From $180 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 ~ Islamorada’s Hidden Gem! This townhouse is located in the heart of Islamorada and offer ...
From $180 per night (USD)VRBO
- From $1237 per night (USD)
Expedia
Penthouse Paradise | Developer Unit w\/ 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 $1237 per night (USD)Expedia
- From $1500 per night (USD)
VRBO
Direct Ocean Front Estate, Private Beach, HUGE Salt Pool\/Hottub, Private Basin!!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Oceanfront Estate on 3.5 PRIVATE. Tropical Acres in the Heart Of Islamorada. Nothing like this rental in the Keys. Feat ...
From $1500 per night (USD)VRBO
- From $149 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 $149 per night (USD)VRBO
- From $150 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 $150 per night (USD)VRBO
- From $500 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 $500 per night (USD)VRBO
- From $160 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 $160 per night (USD)VRBO
- From $448 per night (USD)
VRBO
Charming 2 Bedroom Ground Level Home with Bay Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $448 per night (USD)VRBO
- From $1226 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 $1226 per night (USD)VRBO
- From $625 per night (USD)
VRBO
*Searenity Beach House* - Ocean Front Home with Views of the Atlantic Ocean
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Beautiful home, facing ocean views indoors and out! The house affords breath taking views of the atlantic ocean, Snorke ...
From $625 per night (USD)VRBO
- From $198 per night (USD)
VRBO
Wonderful 2 Bedroom Condo with Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $198 per night (USD)VRBO
- From $128 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 $128 per night (USD)VRBO
- From $675 per night (USD)
VRBO
Islamorada Island Getaway
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Relax and enjoy the Florida Keys lifestyle and outdoor living with full wrap around terraces. PLEASE NOTE: 28 night min ...
From $675 per night (USD)VRBO
- From $250 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 $250 per night (USD)Expedia
- From $275 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 $275 per night (USD)VRBO
- From $1150 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 $1150 per night (USD)VRBO
- From $623 per night (USD)
VRBO
Waterfront | Pool | Downtown Islamorada | Little Basin Villas | Conch Villa 6
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Conch Villa #6 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of t ...
From $623 per night (USD)VRBO
- From $264 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 $264 per night (USD)Expedia
- From $1850 per night (USD)
VRBO
Brand New Unique Deep Water Gulf Front Estate. Beach, Pool, Hot tub and docks
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This is a brand new house. Just completed August 2014 This unique Gulf Front property is located among Gumbo Limbo, M ...
From $1850 per night (USD)VRBO
- From $681 per night (USD)
Expedia
Waterfront | Pool | Walk to Restaurants | Little Basin Villas | Bay Villa 7
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Villa #7 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of the ...
From $681 per night (USD)Expedia
- From $569 per night (USD)
VRBO
Waterfront | Pool | Downtown Islamorada | Little Basin Villas | Conch Villa 4
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Conch Villa #4 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of t ...
From $569 per night (USD)VRBO
- From $410 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 $410 per night (USD)VRBO
- From $396 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 $396 per night (USD)VRBO
- From $245 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 $245 per night (USD)VRBO
- From $650 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 $650 per night (USD)VRBO
- From $514 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 $514 per night (USD)VRBO
- From $343 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 $343 per night (USD)VRBO
- From $448 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 $448 per night (USD)VRBO
- From $210 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 $210 per night (USD)VRBO
- From $486 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 $486 per night (USD)VRBO
- From $128 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 $128 per night (USD)VRBO
- Click For Pricing
VRBO
Islamorada Home with Direct Access to Ocean and Bay
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful 4 bedroom/ 3.5 bathroom home has a 70' dock. Its canal leads straight out to Snake Creek with direct Ocea ...
Click For PricingVRBO
- From $164 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 $164 per night (USD)VRBO
- From $164 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 $164 per night (USD)VRBO
- From $395 per night (USD)
VRBO
WOW!! WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CLEAN-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 $395 per night (USD)VRBO
- From $200 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 $200 per night (USD)VRBO
- From $1485 per night (USD)
VRBO
Southern Diversion Estate Islamorada see our winter discounts
- 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 $1485 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Stunning Oceanview Townhome \n
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Experience total seclusion in this ten-unit oceanfront complex called Port of Call, nestled along Millionaire's Row in I ...
From $300 per night (USD)VRBO
- From $170 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 $170 per night (USD)VRBO
- From $684 per night (USD)
Expedia
Pool | Waterfront | Downtown Islamorada | Little Basin Villas | Bay Villa 8
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Villa #8 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of the ...
From $684 per night (USD)Expedia
- From $587 per night (USD)
VRBO
Pool | Sunsets | Walk to Art District | Little Basin Villas | Key Lime Villa 3
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Key Lime Villa #3 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart o ...
From $587 per night (USD)VRBO
- From $453 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 $453 per night (USD)VRBO
- From $598 per night (USD)
VRBO
Charming Beach Front Home in Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
113 Sunset Drive - Come and stay in this adorable "beachy backyard" home located on the crystal-clear Atlantic Ocean! Th ...
From $598 per night (USD)VRBO
- From $371 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 $371 per night (USD)Expedia
- From $1357 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 $1357 per night (USD)VRBO
- From $995 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 $995 per night (USD)Expedia