Islamorada Rentals
From $314 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 $314 per night (USD)VRBO
From $307 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 $307 per night (USD)VRBO
From $307 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 $307 per night (USD)VRBO
From $314 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 $314 per night (USD)VRBO
From $305 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 $305 per night (USD)VRBO
From $334 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 $334 per night (USD)VRBO
From $265 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 $265 per night (USD)VRBO
From $356 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 $356 per night (USD)VRBO
From $314 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 $314 per night (USD)VRBO
From $334 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 $334 per night (USD)VRBO
From $255 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 $255 per night (USD)VRBO
From $255 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 $255 per night (USD)VRBO
From $263 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 $263 per night (USD)VRBO
From $255 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 $255 per night (USD)VRBO
From $335 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 $335 per night (USD)VRBO
From $335 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 $335 per night (USD)VRBO
From $290 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 $290 per night (USD)VRBO
From $290 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 $290 per night (USD)VRBO
From $335 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 $335 per night (USD)VRBO
From $294 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 $294 per night (USD)VRBO
From $459 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 $459 per night (USD)VRBO
From $406 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 $406 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 $536 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 $536 per night (USD)VRBO
From $550 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 $550 per night (USD)VRBO
From $822 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 $822 per night (USD)VRBO
From $1071 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 $1071 per night (USD)VRBO
From $831 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 $831 per night (USD)VRBO
From $1144 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 $1144 per night (USD)VRBO
From $550 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 $550 per night (USD)VRBO
From $831 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 $831 per night (USD)VRBO
From $550 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 $550 per night (USD)VRBO
From $822 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 $822 per night (USD)VRBO
From $1071 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 $1071 per night (USD)VRBO
From $1144 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 $1144 per night (USD)VRBO
From $1071 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 $1071 per night (USD)VRBO
From $831 per night (USD)VRBO
Convenient Location! 3 Convenient Units, Pool, Pet-Friendly, 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 $831 per night (USD)VRBO
From $536 per night (USD)VRBO
Pets are Allowed Here! 2 Comfortable Units, Free Breakfast, Parking, 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 $536 per night (USD)VRBO
From $536 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 $536 per night (USD)VRBO
From $386 per night (USD)VRBO
108 Anglers Reef Islamorada 31' BOAT SLIP AVAILABLE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful Key West Style home 2 BR 2 BA (en suites) + 1 HF BA Sleeps 6 Islamorada Vacation rental #24-3018 108 Anglers ...
From $386 per night (USD)VRBO
From $516 per night (USD)VRBO
Feel the breeze of the keys
- Bedrooms:
- 3
- 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)Expedia
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)Expedia
From $408 per night (USD)VRBO
The Nest Villa & Marina with boat ramp, sun terrace, water views. Pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If you are looking for peace and tranquility or somewhere to launch and dock your boat for the best fishing and diving i ...
From $408 per night (USD)VRBO
From $205 per night (USD)VRBO
Coconut Palm Inn Beachfront Hideway's Harborview House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 bedroom, 2 bathroom Key Largo vacation rental's layout is a perfect setting to enjoy the Florida Keys on your ter ...
From $205 per night (USD)VRBO
From $442 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 $442 per night (USD)VRBO
From $199 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 $199 per night (USD)Expedia
From $897 per night (USD)VRBO
The Villa by the Bay, Islamorada FL private plunge pool, boat dockage & sunsets
- Bedrooms:
- 3
- 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 $897 per night (USD)VRBO
From $421 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 $421 per night (USD)VRBO
From $196 per night (USD)VRBO
Zesty Lower Matecumbe Condo with Private Beach & Dockage
- Bedrooms:
- 1
- 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 $196 per night (USD)VRBO
From $478 per night (USD)Expedia
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 $478 per night (USD)Expedia
From $244 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 $244 per night (USD)VRBO
From $603 per night (USD)VRBO
Immaculate Islamorada Home with 100' of Dockage, Pool & More!
- Bedrooms:
- 2
- 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 $431 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 $431 per night (USD)VRBO
From $342 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 $342 per night (USD)VRBO
From $431 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 $431 per night (USD)VRBO
From $342 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 $342 per night (USD)VRBO
From $431 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 $431 per night (USD)VRBO
From $340 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 $340 per night (USD)VRBO
From $456 per night (USD)VRBO
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)VRBO
From $468 per night (USD)Expedia
Best location in downtown Islamorada. 2 Houses with Beach access!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 18
Unbelievable location in Islamorada Florida Keys! You have beach access and boat trailer parking. This listing is for 2 ...
From $468 per night (USD)Expedia
From $184 per night (USD)VRBO
OCEAN FRONT TOWN HOUSE with breath taking views from all 3 balconies.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We are delighted to offer this 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! Breathtaking views off of all 3 balco ...
From $184 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:
- 10
- 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)VRBO
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)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 $937 per night (USD)VRBO
Oceanfront Condo @ Maison Matecumbe - 3 bedrooms overlooking pool, Ocean & beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your dream vacation home in Islamorada, the jewel of the Florida Keys! This 3-bedroom condo boasts a prime lo ...
From $937 per night (USD)VRBO
From $607 per night (USD)VRBO
Venetian Shores 20K boat lift 28 day Minimum, ...
- 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 $607 per night (USD)VRBO
From $370 per night (USD)VRBO
Private End Unit in Anglers Reef Resort Islamorada Boat Slip, Ocean Views & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Completely Renovated Home - Among the Largest Floorplans in Anglers Reef! Anglers Reef is a gated community fully equip ...
From $370 per night (USD)VRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
From $1221 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 $1221 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 $955 per night (USD)VRBO
Venetian Shores 5BR/7BA Home with Pool, Spa & Boat Lifts
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Rare Summer Openings! Your Private Resort Awaits in Islamorada If you’ve been dreaming of an island escape with all th ...
From $955 per night (USD)VRBO
From $267 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 $267 per night (USD)Expedia
From $771 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 $771 per night (USD)VRBO
From $208 per night (USD)VRBO
New to the Market: Summer Sea 207
- Bedrooms:
- 1
- 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 $208 per night (USD)VRBO
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $278 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 $278 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 $727 per night (USD)Expedia
Waterfront Home With Swimming Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
PROPERTY NAME: Conch Bar South 194 Indian Mound Trail, Plantation Key, Florida LOCATION: Bayside home located at the mo ...
From $727 per night (USD)Expedia
From $397 per night (USD)VRBO
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 $397 per night (USD)VRBO
From $478 per night (USD)VRBO
Charming Angler's Reef Home with Pool, Dock, Beach & Ocean View
- Bedrooms:
- 2
- 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 $478 per night (USD)VRBO
From $559 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 $559 per night (USD)VRBO
From $496 per night (USD)VRBO
\"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)VRBO
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 $759 per night (USD)VRBO
Venetian Shores 5BR/7BA Home with Pool, Spa & Boat Lifts
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
Rare Summer Openings! Your Private Resort Awaits in Islamorada We’ve just had a rare cancellation at one of our most s ...
From $759 per night (USD)VRBO
From $1877 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 $1877 per night (USD)VRBO
From $138 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 $138 per night (USD)VRBO
From $512 per night (USD)VRBO
3 Bedroom Islamorada Condo w/ 30' Boat Slip & Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Mother Ocean! This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfec ...
From $512 per night (USD)VRBO
From $649 per night (USD)Expedia
Lush tropical plantings in a gated compound located directly on the Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
PROPERTY NAME: Little Bay Cottage 82246 Overseas Highway, Islamorada, Florida LOCATION: Cottage located directly on th ...
From $649 per night (USD)Expedia
From $462 per night (USD)VRBO
Cozy Islamorada retreat!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our Islamorada home is your home away from home! Our home is in a private and quiet, gated community on the bay side, w ...
From $462 per night (USD)VRBO
From $652 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 $652 per night (USD)VRBO
From $321 per night (USD)VRBO
Tropical Paradise Retreat in Islamorada! Pool, Pet-friendly, 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 $321 per night (USD)VRBO
From $321 per night (USD)VRBO
Comfort and Convenience! Swimming Pool, Free Parking, Pets Allowed!
- 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 $321 per night (USD)VRBO
From $321 per night (USD)VRBO
Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, 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 $321 per night (USD)VRBO
From $319 per night (USD)VRBO
Cozy Islamorada home! Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this beautiful and Newley renovated cozy Islamorada home! This home is a couple blocks away from the famous A ...
From $319 per night (USD)VRBO
From $129 per night (USD)VRBO
Pool, Beach and Tennis Court! Fishing, swimming and relaxation!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Take it easy at this unique and tranquil getaway. Enjoy this well equipped 2 bedroom, 2 bath home. Enjoy beautiful suns ...
From $129 per night (USD)VRBO
From $420 per night (USD)Expedia
Island Sanctuary Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored ...
From $420 per night (USD)Expedia
From $7046 per night (USD)VRBO
Island Beach House Oasis Your Memory Maker awaits
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
***Notwithstanding anything in the rates page the minimum renal is 28 days*** There is luxury, luxury and unrivaled, an ...
From $7046 per night (USD)VRBO
From $546 per night (USD)VRBO
Canal front home in Venetian Shores. Perfect for families . A boater's paradise!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 16
This canal front home is located in the prestigious Venetian Shores neighborhood. The perfect location right off of Snak ...
From $546 per night (USD)VRBO