Islamorada Rentals
From $471 per night (USD)VRBO
Premium Units w\/ Ocean Views & Balcony! Marina, Pets Allowed, Beach Access!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $471 per night (USD)VRBO
From $358 per night (USD)VRBO
Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $358 per night (USD)VRBO
From $432 per night (USD)VRBO
Spacious Villa! Private Beach Access, Pets Allowed, Bike Rentals!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $432 per night (USD)VRBO
From $424 per night (USD)VRBO
Classic Villa w\/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $424 per night (USD)VRBO
From $424 per night (USD)VRBO
Family Fun at Islamorada! Large Villa, FREE Parking & Breakfast, Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $424 per night (USD)VRBO
From $432 per night (USD)VRBO
Sportfishing in Florida Keys! Large Unit w\/ Private Beach Access! Pool, Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $432 per night (USD)VRBO
From $424 per night (USD)VRBO
Relax and Unwind Near Robbie's of Islamorada! FREE Parking & Breakfast, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $424 per night (USD)VRBO
From $430 per night (USD)VRBO
Sportfishing in Florida Keys! Elegant Villa w\/ Beach Access and Pool! Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $430 per night (USD)VRBO
From $358 per night (USD)VRBO
Kayak in Florida Keys! Seaside Villa w\/ Patio! Marina, Pool, Kayak
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $358 per night (USD)VRBO
From $471 per night (USD)VRBO
Spacious Unit w\/ Kitchenette & Balcony! Marina, Pets Allowed, Bike Rentals!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $471 per night (USD)VRBO
From $432 per night (USD)VRBO
Snorkeling in Islamorada! Premium Villa, Bike Rentals & Water Sports Equipment!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $432 per night (USD)VRBO
From $430 per night (USD)VRBO
Steps to Windley Key! Pet-friendly Villa! Marina, FREE Parking, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $430 per night (USD)VRBO
From $370 per night (USD)VRBO
Beach View Unit in Islamorada! Pets Allowed, Parking, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $370 per night (USD)VRBO
From $370 per night (USD)VRBO
Snorkeling & Kayaking Beach Resort! Seaside Villa w\/Patio! Marina, Pool, Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $370 per night (USD)VRBO
From $358 per night (USD)VRBO
Discover Florida Keys! Seaside Villa w\/ Patio! Marina, Pool, Parking, Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $358 per night (USD)VRBO
From $370 per night (USD)VRBO
Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $370 per night (USD)VRBO
From $421 per night (USD)VRBO
Seaside Villas w\/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $421 per night (USD)VRBO
From $421 per night (USD)VRBO
Steps to Windley Key! 3 Pet-friendly Units w\/ Balcony! Beach Access & Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $421 per night (USD)VRBO
From $393 per night (USD)VRBO
Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $393 per night (USD)VRBO
From $393 per night (USD)VRBO
Snorkel and Kayak in Islamorada! Unit w\/ Balcony! Pets Allowed, FREE Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $393 per night (USD)VRBO
From $421 per night (USD)VRBO
Exquisite Unit w\/ Balcony and Kitchenette! Pool Pets Allowed, Bike Rental!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $421 per night (USD)VRBO
From $393 per night (USD)VRBO
Florida Keys Tour! Private Beach Access with Marina! Pets Allowed, FREE Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $393 per night (USD)VRBO
From $489 per night (USD)VRBO
Light + Bright Islamorada Pool Home with Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Islamorada Reef Home, a light and bright Islamorada pool home with dockage. You’ll feel right at home in th ...
From $489 per night (USD)VRBO
From $780 per night (USD)Expedia
Canal-front home with private dock, wraparound deck, & central AC - snowbirds OK
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Plaza Del Sol Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $780 per night (USD)Expedia
From $558 per night (USD)VRBO
Waterfront Luxury Bayside Home, Maritime Modern
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
There is something for everyone in your group within reach. If you are a boater, the open bay is only a moment's boat ri ...
From $558 per night (USD)VRBO
From $745 per night (USD)VRBO
Make Your Trip More Enjoyable! 2 Convenient Units, Pets Allowed, Onsite Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $745 per night (USD)VRBO
From $730 per night (USD)VRBO
Better Choice for your Vacation! 2 Pet-Friendly Units, Free Breakfast, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $730 per night (USD)VRBO
From $1125 per night (USD)VRBO
Everything You Need For The Perfect Vacation! 3 Convenient Units, FREE Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $1125 per night (USD)VRBO
From $1125 per night (USD)VRBO
Dive Into Your Dream Vacation! 3 Spacious Units, Onsite Pool, FREE Breakfast!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $1125 per night (USD)VRBO
From $1055 per night (USD)VRBO
Comfort & Convenience, 3 Classy Units, Free Breakfast, Free Parking, Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $1055 per night (USD)VRBO
From $1513 per night (USD)VRBO
Making The Best Memories Along The Way! 4 Comfortable Units, FREE Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $1513 per night (USD)VRBO
From $730 per night (USD)VRBO
Vacation At its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $730 per night (USD)VRBO
From $1055 per night (USD)VRBO
Best Place to Stay in Florida! 3 Pet-Friendly Units, Free Breakfast, Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $1055 per night (USD)VRBO
From $730 per night (USD)VRBO
Get Ready for Blissful Getaway! 2 Relaxing Units, Onsite Pool, Free Breakfast
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $730 per night (USD)VRBO
From $1125 per night (USD)VRBO
3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $1125 per night (USD)VRBO
From $1564 per night (USD)VRBO
Snorkeling & Kayaking Beach Resort! Seaside Villa w\/Patio! Marina, Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $1564 per night (USD)VRBO
From $1513 per night (USD)VRBO
Your Home Away From Home! 4 Relaxing Units, FREE Parking, Onsite Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $1513 per night (USD)VRBO
From $745 per night (USD)VRBO
Escape The Hustle and Bustle! 2 Classy Units, Free Parking, Onsite Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $745 per night (USD)VRBO
From $1513 per night (USD)VRBO
Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $1513 per night (USD)VRBO
From $516 per night (USD)VRBO
Feel the breeze of the keys
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
**HOUSE HAS BEEN RENOVATED AND PICTURES TO COME** Perfect Vacation Home in Islamorada, the center of the Keys Island. T ...
From $516 per night (USD)VRBO
From $267 per night (USD)VRBO
Best Location in Islamorada!! Beach access - Boat trailer parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Gorgeous and highly appointed luxury Island villa with beach access. You are right in the middle of it all with this per ...
From $267 per night (USD)VRBO
From $399 per night (USD)VRBO
The Nest Villa & Marina with boat ramp, sun terrace, water views & pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The "Nest" villa is one of only seven units nestled on a one acre native tropical hammock directly on Florida Bay with s ...
From $399 per night (USD)VRBO
From $702 per night (USD)VRBO
Islamorada Oasis, Luxurious 4 bedroom 3 bath home. Heated pool! Boat Lift option
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Islamorada Oasis is designed for families and outdoor lovers! Inside and out, its ready for entertaining and keys styl ...
From $702 per night (USD)VRBO
From $222 per night (USD)Expedia
Mercy’s waterfront piece of paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our home is a unique place situated in the best location in the mid/upper keys. A single family property, all refurbishe ...
From $222 per night (USD)Expedia
From $424 per night (USD)VRBO
Sit back and relax in this beautiful Islamorada Pool home!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Put your mail on hold, your new Islamorada address is waiting! Sit back and relax in this beautiful Islamorada Pool ho ...
From $424 per night (USD)VRBO
From $1074 per night (USD)Expedia
The Villa by the Bay, Islamorada FL private plunge pool, boat dockage & sunsets
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Take your heart, family & fishing gear to the blissful Villa by the Bay! Quaint gated 8 homes; Coral Cove is centrally l ...
From $1074 per night (USD)Expedia
From $437 per night (USD)VRBO
Fantastic Bayside Townhouse
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Fantastic gated Bayside townhouse with all the bells and whistles. Excellant location with everything you need to have a ...
From $437 per night (USD)VRBO
From $212 per night (USD)VRBO
Zesty Lower Matecumbe Condo with Private Beach & Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
It's not every day that you come across a rental like this. This delightful and fun 2 bedroom, 1.5 located in Lower Mate ...
From $212 per night (USD)VRBO
From $455 per night (USD)VRBO
Bungalow #5 - 2 Bed\/1 Bath & Pool in Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, w ...
From $455 per night (USD)VRBO
From $2297 per night (USD)Expedia
Luxurious PH 5BR 3.5BA Gym\/ Pool & Jacuzzi\/ Sauna
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to your luxurious retreat in Islamorada! Experience the epitome of luxury living at our stunning condo located a ...
From $2297 per night (USD)Expedia
From $139 per night (USD)VRBO
Keys Getaway – 2 Bikes, Heated Pool, Small Beach & Sunset Dock Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Your Florida Keys Getaway – A Slice of Paradise in Islamorada Welcome to our beautiful 2-bedroom, 2-bathroom t ...
From $139 per night (USD)VRBO
From $603 per night (USD)VRBO
Immaculate Islamorada Home with 100' of Dockage, Pool & More!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This tropical oasis has everything you need and more for the perfect summer vacation! Nestled in the highly sought-aft ...
From $603 per night (USD)VRBO
From $572 per night (USD)VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $572 per night (USD)VRBO
From $424 per night (USD)VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $424 per night (USD)VRBO
From $572 per night (USD)VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $572 per night (USD)VRBO
From $424 per night (USD)VRBO
Prime Location! Onsite Pool, Free Breakfast, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $424 per night (USD)VRBO
From $572 per night (USD)VRBO
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $572 per night (USD)VRBO
From $424 per night (USD)VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $424 per night (USD)VRBO
From $355 per night (USD)VRBO
Upscale Waterfront Home 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 $355 per night (USD)VRBO
From $456 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 $456 per night (USD)Expedia
From $254 per night (USD)VRBO
Best location in downtown Islamorada. Beach access and boat trailer parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Unbelievable location in Islamorada Florida Keys! You have beach access and boat trailer parking. Close enough to walk a ...
From $254 per night (USD)VRBO
From $291 per night (USD)VRBO
OCEAN FRONT TOWN HOUSE with breath taking views from all 3 balconies.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
We are delighted to offer this 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! Breathtaking views off of all 3 balco ...
From $291 per night (USD)VRBO
From $568 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 $568 per night (USD)VRBO
From $3453 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 $3453 per night (USD)VRBO
From $438 per night (USD)VRBO
Pet Friendly 2 Bedroom in Venetian Shores Sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
The Salty B is located in the popular neighborhood of Venetian Shores! Canal front home on Snake Creek gives you fast ac ...
From $438 per night (USD)VRBO
From $383 per night (USD)Expedia
Fabulous Island Getaway! Easy access to Florida Bay, Private Beach, Elevator
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy watching the ospreys and manatees from the dock at this beautiful Port Antigua home on Biscayne Blvd. You have acc ...
From $383 per night (USD)Expedia
From $448 per night (USD)VRBO
Keys Villa--Islamorada private beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two bedroom "gem" in the Florida Keys!! Enjoy our sand beach, beautiful sunsets, fish from our docks, swim in our pool, ...
From $448 per night (USD)VRBO
From $901 per night (USD)VRBO
Maison Matecumbe.... the heart of Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Maison Matecumbe #301 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centra ...
From $901 per night (USD)VRBO
From $184 per night (USD)VRBO
Charming Condo in Paradise!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Take a break & unwind at this charming Islamorada gem! Let this 1/1 bright & homey condo be your needed getaway to parad ...
From $184 per night (USD)VRBO
From $372 per night (USD)Expedia
Tropical Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful bayside villa in Islamorada. Sandy beach, fishing dock, pool, tennis court and boat slip for up to 25 ft boat ...
From $372 per night (USD)Expedia
From $258 per night (USD)VRBO
Stunning Penthouse 3 bedroom Apartment, New
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Stunning 3 bedroom Penthouse is absolutely stunning! The photos do not due justice to the amazing ceiling, Livingro ...
From $258 per night (USD)VRBO
From $453 per night (USD)VRBO
Beautiful Keys Style Retreat - with bonus room, private pool and private dock.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Experience paradise in our stunning 2-story, 2-bedroom, 3-bathroom rental property located in a peaceful residential nei ...
From $453 per night (USD)VRBO
From $512 per night (USD)VRBO
Venetian Shores 20K boat lift 28 day Minimum, ..August Cancellation now open....
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Venetian shores 4 bedroom 3 bath, pool, hotub, 300lbs ice machine with 20K boat lift, Master has a double walk-in shower ...
From $512 per night (USD)VRBO
From $206 per night (USD)VRBO
Beautiful 2 Bedroom 2 Bath Condo Coral Harbour Islamorada - Marina, Pool, Gated
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This special place is close to everything, making it easy to plan your visit. Beautiful updated 2 bedroom 2 bath watervi ...
From $206 per night (USD)VRBO
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A place in paradise!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This unique home gives you the quintessential keys experience. Nestled in a small, quaint gated, private community with ...
Click For PricingVRBO
From $215 per night (USD)VRBO
Top Floor, Bay View, Dockage, Vacation Today!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come enjoy the breathtaking views this condo has to offer. Located in the Futura Yacht Club community, located at mile ...
From $215 per night (USD)VRBO
From $528 per night (USD)VRBO
New Rental! Beautiful canal pool home with dockage!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Cozy, canal front, pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Ba ...
From $528 per night (USD)VRBO
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Comfy Townhome at Executive Bay Club - Marina, Pool, and Tennis!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Enjoy this stylishly remodeled townhome in the Heart of Islamorada at Executive Bay Club. This 7-guest retreat features ...
Click For PricingExpedia
Click For PricingVRBO
PARADISE FOUND! 3 BD townhome in BEACHFRONT Executive Bay Club in Islamorada, FL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise Found! Enjoy fantastic sunsets in an updated 1400 sq. ft. townhouse in beautiful Executive Bay Club, on mile ma ...
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From $485 per night (USD)Expedia
Mojito Breeze Getaway
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Beachy but elegant, close to mainland FL, sleeps 12 comfortably, timeless tropical getaway, plenty of room Nice, quiet ...
From $485 per night (USD)Expedia
From $1260 per night (USD)VRBO
The Sailfish House ~ 4 Bed \/ 4 Bath Luxury Oceanfront Home in Islamorada!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the “Sailfish House” at Tarpon Point! Soak up the sun and take in the spectacular views at this opulent 4 be ...
From $1260 per night (USD)VRBO
From $508 per night (USD)VRBO
4BR waterfront home with POOL, boat slip with straight shot to Alligator Reef!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Island Villa Rental Properties offers Seas The Day in Islamorada, Florida Keys. Seas the Day is a fun, 4 bedroom house ...
From $508 per night (USD)VRBO
From $843 per night (USD)VRBO
Spectacular Coastal Paradise with outstanding outdoor living spaces
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to the islands in your own private resort. This Florida Keys home feels like your own private tropical oasis loc ...
From $843 per night (USD)VRBO
From $406 per night (USD)Expedia
Islamorada Key Waterfront House w\/ Private Boat Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy 2/2 Waterfront home located in the Best Location. Two King beds . High speed Wifi, Smart TVs, BBQ, Great living r ...
From $406 per night (USD)Expedia
From $961 per night (USD)VRBO
ISLAMORADA DREAM HOUSE
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ONE-OF-A-KIND VACATION EXPERIENCE. You will never want to leave. Large open space, dining, kitchen and living room. Priv ...
From $961 per night (USD)VRBO
From $202 per night (USD)VRBO
New to the Market: Summer Sea 207
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summer Sea Condo #207: Modern and spectacularly updated 2nd floor unit with private balcony just steps away from the sta ...
From $202 per night (USD)VRBO
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Bay view villa in Islamorada, palm trees, shade trees and two private porches
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Unwind with a Bay view, approx. 1 hour from Miami airport. Access to mini beach, great sunsets and boat ramp, swimming ...
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From $218 per night (USD)Expedia
This condo is located in one of Islamorada's most prestigious condo complexes.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY NAME: Beacon Reef #307 83201 Old Highway, Islamorada, Florida LOCATION: Ocean side Condo MINIMUM STAY: 28 Day ...
From $218 per night (USD)Expedia
From $340 per night (USD)VRBO
Beautifully remodeled roomy single family stilt home,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
PROPERTY NAME: West Plaza 63 West Plaza Del Lago, Islamorada, FL LOCATION: Bayside House MINIMUM STAY: 28 Days, All s ...
From $340 per night (USD)VRBO
From $374 per night (USD)Expedia
Beautiful Water Views from every room in the House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
PROPERTY NAME: Harbor House 101 San Juan Dr., Islamorada, FL LOCATION: Bayside Canal home located in the Upscale Veneti ...
From $374 per night (USD)Expedia
From $624 per night (USD)VRBO
Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
PROPERTY NAME: Pelican Landing 60 West Plaza Del Lago, Islamorada, FL LOCATION: Bayside Private Home in the neighborhoo ...
From $624 per night (USD)VRBO
From $466 per night (USD)VRBO
Charming Angler's Reef Home with Pool, Dock, Beach & Ocean View
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Islamorada’s Finest Oceanfront Gated Community Soak up the sun and enjoy the ocean breeze from this charming ...
From $466 per night (USD)VRBO
From $649 per night (USD)VRBO
Boaters Paradise - Luxury Islamorada waterfront home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stunning waterfront Islamorada house on a corner lot with direct access to the Bay and 5 minutes from the Atlantic Ocean ...
From $649 per night (USD)VRBO
From $496 per night (USD)Expedia
\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the ...
From $496 per night (USD)Expedia
From $286 per night (USD)VRBO
Bayside Boater's Paradise-great for Snowbirds-60 d min stay- add 1:1private unit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This 2 bedroom- 2 bath, fully-equipped kitchen waterfront home on a deep canal offers a 75 ft-wide frontage dock with 38 ...
From $286 per night (USD)VRBO
From $785 per night (USD)VRBO
Venetian Shores 5BR\/7BA Home with Pool, Spa & Boat Lifts Available July & Aug 25
- Bedrooms:
- 8
- Bathrooms:
- 5
- Sleeps:
- 10
September 2024 special 40% discount 5 bedroom 7 bath in Venetian shores in the Florida Keys, Pool and Hot Tub with a hu ...
From $785 per night (USD)VRBO
From $392 per night (USD)VRBO
Beautiful Lower Unit with Dockage, Pool and Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
PROPERTY NAME: Parrot Eyes 130 Plantation Ave. Tavernier, Florida 33070 LOCATION: Bayside Canal home located in Taverni ...
From $392 per night (USD)VRBO
From $417 per night (USD)Expedia
Beautiful Upper Unit with Dockage, Pool and Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY NAME: Parrot Eyes 130 Plantation Ave. Tavernier, Florida 33070 LOCATION: Bayside Canal home located in Taverni ...
From $417 per night (USD)Expedia
From $784 per night (USD)VRBO
Beautiful Home with Dockage, Pool and Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
PROPERTY NAME: Parrot Eyes 130 Plantation Ave. Tavernier, Florida 33070 LOCATION: Bayside Canal home located in Taverni ...
From $784 per night (USD)VRBO
From $1698 per night (USD)VRBO
Ocean & Pool Front Maison Residences, on sandy beach, heated pool in Islamorada
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
FLORIDA KEYS BEACHFRONT VACATION RENTALS AT MAISON RESIDENCES While staying at the Maison Residences, you’ll have the c ...
From $1698 per night (USD)VRBO