Islamorada Rentals
- From $1687 per night (USD)
VRBO
Indulge in Home Like Comfort! 4 Pleasant Units, Free Parking, Onsite Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $1687 per night (USD)VRBO
- From $1610 per night (USD)
VRBO
A Place You'll Surely Enjoy! 4 Relaxing Units, Free Parking, Onsite Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $1610 per night (USD)VRBO
- From $367 per night (USD)
VRBO
Comfort and Relaxation! Free Parking, Minutes to History of Diving Museum
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $367 per night (USD)VRBO
- From $1442 per night (USD)
VRBO
Enjoy a Hassle-Free Stay! 4 Comfortable Units, Onsite Pool, Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $1442 per night (USD)VRBO
- From $1683 per night (USD)
VRBO
Make Your Trip More Enjoyable! 4 Family-friendly Units, Pets Allowed, Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $1683 per night (USD)VRBO
- From $1610 per night (USD)
VRBO
Your Home Away From Home! 4 Convenient Units, Free Parking, Pets Allowed
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $1610 per night (USD)VRBO
- Click For Pricing
Expedia
4 Bedroom Single_family 441709 by Houzlet
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy Bay Views from the comfort of your own home! Situated on 2 lots directly across from Homeowners Park (w/ boat ramp ...
Click For PricingExpedia
- From $577 per night (USD)
VRBO
Why watch the Sunrise when you have a Mangrove Sunset
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning pool home is nestled along a private canal with convenient dockage and quick access to the bay! This lu ...
From $577 per night (USD)VRBO
- From $725 per night (USD)
VRBO
Adventure Awaits in Islamorada! 2 Modern Units, Beach, Pool, Pet-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $725 per night (USD)VRBO
- From $725 per night (USD)
VRBO
Coastal Living in Islamorada! 2 Comfortable Units, Swimming Pool, Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $725 per night (USD)VRBO
- From $1087 per night (USD)
VRBO
Tropical Getaway in Islamorada! 3 Modern Units, Beach, Swimming Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $1087 per night (USD)VRBO
- From $1087 per night (USD)
VRBO
A New Day in Paradise in Islamorada! 3 Relaxing Units, Swimming Pool, Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $1087 per night (USD)VRBO
- From $1082 per night (USD)
VRBO
Discover the Keys in Islamorada! 3 Convenient Units, Beach, Swimming Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $1082 per night (USD)VRBO
- From $782 per night (USD)
VRBO
Relax and Recharge in Islamorada! 2 Relaxing Units, Pets Allowed, Outdoor Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $782 per night (USD)VRBO
- From $782 per night (USD)
VRBO
Charming Escape in Islamorada! 2 Modern Units, Swimming Pool, Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $782 per night (USD)VRBO
- From $421 per night (USD)
VRBO
Home Away from Home in Islamorada! Pets Allowed, Free Parking, Outdoor Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $421 per night (USD)VRBO
- From $802 per night (USD)
VRBO
Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $802 per night (USD)VRBO
- From $454 per night (USD)
VRBO
Your Blissful Haven in Islamorada! Beach, Swimming Pool, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $454 per night (USD)VRBO
- From $408 per night (USD)
VRBO
Your Charming Stay in Islamorada! Beach, Swimming Pool, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $408 per night (USD)VRBO
- From $408 per night (USD)
VRBO
Discover Islamorada's Treasures! Pets Allowed, Swimming Pool, Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $408 per night (USD)VRBO
- From $517 per night (USD)
VRBO
Your Tropical Home in Islamorada! Pets Allowed, Swimming Pool, Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE SPACE Indulge in a tropical retreat in Islamorada, where unique activities and top-notch service await. Swim with do ...
From $517 per night (USD)VRBO
- From $454 per night (USD)
VRBO
Peaceful Retreat in Islamorada! Pet-friendly, Swimming Pool, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $454 per night (USD)VRBO
- From $454 per night (USD)
VRBO
Peaceful Mornings in Islamorada! Swimming Pool, Beach, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $454 per night (USD)VRBO
- From $802 per night (USD)
VRBO
Your Dream Escape in Islamorada! Pet-friendly Property, Swimming Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $802 per night (USD)VRBO
- From $517 per night (USD)
VRBO
Waterfront Elegance in Islamorada! Beach, Swimming Pool, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $517 per night (USD)VRBO
- From $454 per night (USD)
VRBO
Fun and Sun in Islamorada! Free Parking, Swimming Pool, Pet-friendly Property!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $454 per night (USD)VRBO
- From $421 per night (USD)
VRBO
Relaxation at Its Finest in Islamorada! Free Parking, Swimming Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $421 per night (USD)VRBO
- From $796 per night (USD)
VRBO
Best Place to Unwind! 2 Spacious Units, Free Breakfast, Swimming Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $796 per night (USD)VRBO
- From $306 per night (USD)
VRBO
Newly renovated Port Antigua canal front home with convenient dockage!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Fall Special Rates!! Discounted rates through December, inquire within! Welcome to your dream vacation getaway in the ...
From $306 per night (USD)VRBO
- From $452 per night (USD)
Expedia
Oceanfront luxury home with cabana, pool, hot tub, grill, golf cart, & games
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Adventure Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $452 per night (USD)Expedia
- From $429 per night (USD)
VRBO
Gated Estate Duplex on the Bay with dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
PROPERTY NAME: Little Bay Lower Duplex 82246 Overseas Highway, Islamorada, Florida LOCATION: Duplex located directly on ...
From $429 per night (USD)VRBO
- From $1003 per night (USD)
VRBO
Dive Into Your Dream Vacation! Pool, Pet-friendly, Beachfront Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1003 per night (USD)VRBO
- From $1589 per night (USD)
VRBO
Sunny Vacay! 2 Garden View Units w\/ Kitchenette, Outdoor Pool, Free Parking!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1589 per night (USD)VRBO
- From $794 per night (USD)
VRBO
Beach Adventure! Unit w\/ Kitchenette, Outdoor Pool, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $794 per night (USD)VRBO
- From $1838 per night (USD)
VRBO
Enjoyable Stay! Beachfront Location, With Full Kitchen, Free Parking, Pool!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1838 per night (USD)VRBO
- From $1518 per night (USD)
VRBO
Spacious 3BR Unit w\/ Kitchen Perfect for Groups! w\/ Outdoor Pool, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1518 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Excellent Choice! Pet-friendly Property, Pool, Free Parking Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $375 per night (USD)VRBO
- From $368 per night (USD)
VRBO
Hassle-free Stay! Garden View, w\/ Kitchenette, Steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $368 per night (USD)VRBO
- From $1153 per night (USD)
VRBO
Best Summer Choice! Unit with Full Kitchen, Beachfront, Outdoor Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1153 per night (USD)VRBO
- From $549 per night (USD)
VRBO
Enjoy Relaxing Views! Ocean Front, Pets Allowed, Free Parking Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $549 per night (USD)VRBO
- From $1423 per night (USD)
VRBO
Excellent Choice for Families! Full Kitchen, Pool, Pet-friendly, Free Parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $1423 per night (USD)VRBO
- From $928 per night (USD)
VRBO
Stunning Ocean View! Beachfront Property, w\/ Pool, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $928 per night (USD)VRBO
- From $195 per night (USD)
VRBO
Islamorada Townhome w\/ Pool & Beach Access!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Discover your own tropical paradise at this lovely 2-bedroom, 2-bath vacation rental in Islamorada, FL! Located just ste ...
From $195 per night (USD)VRBO
- From $821 per night (USD)
Expedia
Sandy Beach Cove🏝️🏖️ Private Beach Home and Cottage Compound with Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Relax , Enjoy and Indulge yourself with Family and friends on this Over Half Acre Private Ocean Beach Oasis 🏝️🏖️ with ...
From $821 per night (USD)Expedia
- From $162 per night (USD)
VRBO
Radiant waterfront retreat with remarkable views, patio, tennis court, & grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tollgate Tides Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $162 per night (USD)VRBO
- From $305 per night (USD)
Expedia
Islamorada waterfront villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Resort Style Venetian Shores Home with 70 ft Dock on a 100 foot wide canal Completely remodeled. Two Bedrooms with King ...
From $305 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Islamorada Home on Canal with Private Beach Access\n\/ 4 bedroom 3 bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
This luxurious 4 bedroom, 3 bathroom house offers exceptional opportunity to experience the Florida keys in style with i ...
From $350 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Keys paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Casa Mar is an beautiful 3 bedroom home nestled among tropical foliage. There are three bedrooms and two baths on the h ...
From $225 per night (USD)VRBO
- From $858 per night (USD)
VRBO
Complete Duplex on Gated Bayfront Property
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
PROPERTY NAME: Little Bay Prime 82246 Overseas Highway, Islamorada, Florida LOCATION: Two story Duplex Located Directl ...
From $858 per night (USD)VRBO
- From $429 per night (USD)
Expedia
2nd Floor Duplex on Gated Bayfront Property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROPERTY NAME: Little Bay Upper Duplex 82246 Overseas Highway, Islamorada, Florida LOCATION: Upper Duplex located direc ...
From $429 per night (USD)Expedia
- From $777 per night (USD)
VRBO
Islamorada Keys Waterfront .Pool Luxury Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront Islamorada 4 bedroom 3 bathroom home on the absolute best Waterfront Deep Water Canal w direct ocean access. ...
From $777 per night (USD)VRBO
- From $934 per night (USD)
Expedia
The Villa by the Bay Unit #2
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy a beautiful experience in the heart of Islamorada, the fishing capital of the world! Coral Cove is a gated small c ...
From $934 per night (USD)Expedia
- From $133 per night (USD)
VRBO
Exec Bay townhouse w\/heated pool, marina, beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and experience the beauty and tranquility of the Florida Keys at Executive Bay Club! Enjoy gorgeous views from this ...
From $133 per night (USD)VRBO
- From $552 per night (USD)
Expedia
Grand waterfront estate with 220’ dock, heated pool, & outdoor kitchen
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Casa Del Lago Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $552 per night (USD)Expedia
- From $304 per night (USD)
VRBO
Waterfront home with private pool, bar\/grill, screened patio, & boat access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Waypoint One Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $304 per night (USD)VRBO
- From $125 per night (USD)
Expedia
Capt Craig's 1 Bedroom \/1 Bath Apartment in Islamorada, Florida Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Capt. Craig’s Guest Quarters -The Seahorse is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami Inter ...
From $125 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Brand New Home, Resort Location, Pet Friendly, Oceanview
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This brand new home is sitting quietly behind a controlled access gate with a private balcony overlooking the Atlantic O ...
From $225 per night (USD)VRBO
- From $1000 per night (USD)
Expedia
Spectacular 4 bedroom 4 1\/2 bath villa on Tavernier Creek in Florida Keys.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Incomparable villa directly on Tavernier Creek with immediate access to ocean and bay. Fully fenced and gated. Manatees ...
From $1000 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Brand New Home, Resort Location, Oceanview
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This brand new home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full ...
From $225 per night (USD)VRBO
- From $230 per night (USD)
VRBO
BEAUTIFUL PLACE TO STAY!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
ONE OF "THE BEST" vacation value getaways in the Florida Keys. Packed with amenities, it has access to gulf side docka ...
From $230 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Ocean Harbor Paradise is Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Talk about an Atlantic Ocean View; you've found it! You will fall in love as soon as you enter the gates at Ocean Harbor ...
From $300 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Canal-Front Oasis in the Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to paradise in this stunning 3-bedroom, 2-bathroom vacation home in the heart of the Florida Keys. Situated on a ...
From $275 per night (USD)VRBO
- From $695 per night (USD)
VRBO
Tekeze ~ Relaxed Resort Style Home with 5 Bedrooms, Pool & Dockage
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Tekeze! Short for "Take it Easy,” this oversized 5-bedroom, 4.5-bath home is located on a wide canal in the ...
From $695 per night (USD)VRBO
- From $127 per night (USD)
VRBO
New - beautiful modern W\/beautiful open water view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summer Sea 319 is new to the rental market and recently fully remodeled. Modern, clean with a beautiful open water bay v ...
From $127 per night (USD)VRBO
- From $177 per night (USD)
VRBO
Elegant apartment in the heart of the Islamorada Art District
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In the heart of the Morada Arts District, this spacious 2 bedroom, 2 bath apartment has been totally renovated. The loca ...
From $177 per night (USD)VRBO
- From $1960 per night (USD)
VRBO
Pirate’s Château ~ A Luxurious Islamorada Escape
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Pirate’s Château, where opulence meets Florida Keys charm in one of the most prestigious neighborhoods along ...
From $1960 per night (USD)VRBO
- From $477 per night (USD)
VRBO
Steps Away from the Beach! w/ Outdoor Pool, Free Parking, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $477 per night (USD)VRBO
- From $325 per night (USD)
VRBO
Spectacular Keys home on corner canal, hot tub, tiki hut + much more!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come experience the breathtaking beauty of nature right from your backyard! Relax on the tranquil canal with stunning wa ...
From $325 per night (USD)VRBO
- From $452 per night (USD)
VRBO
Canal front home in Venetian Shores. Perfect for families. A boater's paradise!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This canal front home is located in the prestigious Venetian Shores neighborhood. The perfect location right off of Snak ...
From $452 per night (USD)VRBO
- From $249 per night (USD)
VRBO
Spacious long-term 3\/2 condo rental with boat slip in gated oceanside community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Revel in laid-back luxury island living in the prestigious Coral Harbour Club Condominium. Your unit is a spacious 3 be ...
From $249 per night (USD)VRBO
- From $112 per night (USD)
VRBO
Cute Studio in Summer Sea Condominium
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This cute apartment is new to the rental market. Modern and clean with all the comforts of home with tropical décor, lig ...
From $112 per night (USD)VRBO
- From $494 per night (USD)
VRBO
🌊MOTHER OCEAN🌊 Islamorada Condo w\/ Dockage & Ocean Views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Mother Ocean! This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfec ...
From $494 per night (USD)VRBO
- From $605 per night (USD)
VRBO
Amazing 4 Bedroom Canal Home with Pool and Dockage-Holly's Hideout by FKLR
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Canal Front......Pool......Dockage......Pet friendly......It’s all here at Holly's Hideout! Located in beautiful Tave ...
From $605 per night (USD)VRBO
- From $3333 per night (USD)
VRBO
10 Bedroom Private Ocean Front Estate
- Bedrooms:
- 11
- Bathrooms:
- 10
- Sleeps:
- 22
The Island Palm Estates is a newly constructed estate that includes 2 separate, luxurious homes with all the modern conv ...
From $3333 per night (USD)VRBO
- From $297 per night (USD)
VRBO
Upscale Waterfront Duplex with Private Beach & Dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect upscale Islamorada getaway awaits. Sandy Pointe 113 is a newly renovate home that offers panoramic water vi ...
From $297 per night (USD)VRBO
- From $550 per night (USD)
Expedia
Keys waterfront paradise
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful keys oceanfront home fully equipped . great for entertainment. fishing paradise just a short distance from wor ...
From $550 per night (USD)Expedia
- From $536 per night (USD)
VRBO
Harbor Hideaway | Island style beach house with pool, dockage & bay views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Introducing “Harbor Hideaway!” This charming, island style beach house on Lower Matecumbe Key is the perfect spot for y ...
From $536 per night (USD)VRBO
- From $592 per night (USD)
Expedia
Pool | Pets allowed | Downtown Islamorada | Little Basin Villas | Conch Villa 5
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Conch Villa #5 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of t ...
From $592 per night (USD)Expedia
- From $367 per night (USD)
VRBO
Spacious Home in Islamorada with boat dock, private beach, & Fast
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
**Please contact owner directly via email if dates do not appear on calendar** There is also an in-laws quarter 1/1 avai ...
From $367 per night (USD)VRBO
- From $550 per night (USD)
VRBO
GREAT LOCATION !!! ** White Marlin Beach House, Islamorada FLORIDA KEYS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Contact owner for rates and availability at (305-431-2006). Relax in Islamorada, Florida Keys... 'Sport Fishing Capital ...
From $550 per night (USD)VRBO
- From $1143 per night (USD)
VRBO
Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
OSPREY BAY VILLA! Wonderful Bay front Home in the heart of Islamorada in the fabulous Florida Keys for rent by the week, ...
From $1143 per night (USD)VRBO
- From $148 per night (USD)
VRBO
NEW-Summer Sea - Sweet updated 1B Apartment w\/ Garden View Apt 125
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 bedroom apartment new to the rental market! Modern and updated, this first floor unit has a gorgeous kitchen with stai ...
From $148 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Venetian Shores, Premier Boating Neighborhood in the heart of the Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Three bedroom, 2 bath cottage with pool and Tiki Hut with wet bar. Situated on deep canal in desirable Venetian Shores ...
From $225 per night (USD)VRBO
- From $325 per night (USD)
VRBO
Stunning Bayfront Townhouse with Boat Slip\/ Marina Access - A Luxurious Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Our Cozy Townhouse at Futura Yacht Club! Nestled right by the ocean, our townhouse offers a peaceful escape ...
From $325 per night (USD)VRBO
- From $2571 per night (USD)
VRBO
Caribee Beach House ~ Private Islamorada Beach Estate W\/ Heated Pool & Dockage
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Caribee Beach House! This estate is the perfect mix of old school Islamorada combined with present-day, styl ...
From $2571 per night (USD)VRBO
- From $315 per night (USD)
Expedia
A 57-foot trawler in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in a friendly marina with a restaurants, gift shop, tiki bar, kayaks, jet skis, and charter fishing boats minute ...
From $315 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Boat, Fish, Swim from Your Own 70' Dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come Play! Your 70-foot private dock provides instant access to fun – whether boating, fishing, swimming or relaxing und ...
From $500 per night (USD)VRBO
- From $564 per night (USD)
VRBO
The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital o ...
From $564 per night (USD)VRBO
- From $775 per night (USD)
VRBO
Private Beachfront Paradise<br>
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Village of Islamorada - Vacation Rental License No. VR-110 This home is remodeled every year in some way or form...We tr ...
From $775 per night (USD)VRBO
- From $745 per night (USD)
VRBO
This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3\/2 Sleeps 6
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The single family home has a homey, oceanfront cottage appeal. It sits on the most amazing property with vast ocean vie ...
From $745 per night (USD)VRBO
- From $691 per night (USD)
VRBO
Hidden Gem Duplex in Heart of Islamorada! Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: This truly is a Hidden Gem in the heart of Islamorada. Nestled in the trees just a few steps from one of the mo ...
From $691 per night (USD)VRBO
- From $108 per night (USD)
VRBO
Beautiful 1 bedroom apartment with stunning open water view Apt 317
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Premier 1 bedroom unit with both that stunning direct open water bay view and a view of the pool off the balcony. Beauti ...
From $108 per night (USD)VRBO
- From $999 per night (USD)
VRBO
Oceanfront 1.8 acre Estate on Millionaire's Row, Private Saltwater Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding ...
From $999 per night (USD)VRBO
- From $270 per night (USD)
VRBO
Your Islamorada Vacation dream just became a reality!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
139 Venetian Way - Your Islamorada Winter Vacation dream just became a reality! Brand new to the market, this Venetian S ...
From $270 per night (USD)VRBO
- From $127 per night (USD)
VRBO
Modern one bedroom apartment with beautiful garden view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful, modern updated unit is absolutely beautiful with a private balcony with a wonderful garden view. Homey t ...
From $127 per night (USD)VRBO
- From $307 per night (USD)
VRBO
5 Star Modern Oceanfront Islamorada Townhome on the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Tw ...
From $307 per night (USD)VRBO
- From $261 per night (USD)
VRBO
Relaxing waterfront retreat with boat dock & amazing ocean views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $261 per night (USD)VRBO
- From $2053 per night (USD)
VRBO
Oceanfront Estate with 4 Cozy Cottages
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave o ...
From $2053 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Bayfront Cottage on Private Estate in Heart of Islamorada w\/ POOL, DOCK & BEACH!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Bay View Cottage is one of three homes in Mermaid's Bay Boutique Estate. This private waterfront oasis sprawls 3.5 a ...
From $600 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Quiet Cottage on Bay-Front Estate in Heart of Islamorada w\/ POOL, DOCK & BEACH!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Garden View Cottage is one of three homes at Mermaid's Bay Boutique Estate. This private waterfront oasis sprawls 3. ...
From $600 per night (USD)VRBO