Islamorada Rentals
From $696 per night (USD)VRBO
Harbor Hideaway ~ Island style beach house with pool, dockage & bay views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to Harbor Hideaway! Escape to Harbor Hideaway, your perfect tropical retreat situated on the tranquil shores of ...
From $696 per night (USD)VRBO
From $388 per night (USD)Expedia
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
***June 2022 - Installed a new AC with Germicidal UV light air purifier, which improves air quality by sterilizing mol ...
From $388 per night (USD)Expedia
From $270 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 $270 per night (USD)VRBO
From $1406 per night (USD)VRBO
Islamorada Oceanfront Estate, Pool, Beach Cottages-- Sea Ranch -- Florida Keys
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Island Villa Rental Properties offers this two adorable, private cottages right on the Atlantic Ocean. Located in the he ...
From $1406 per night (USD)VRBO
From $318 per night (USD)VRBO
Ocean View with protected dock on lagoon with private boat ramp
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Large 3/2 with ground level carport. Lagoon side screened porch 50' x 10'. Terrace on Ocean side is open. Boat acces ...
From $318 per night (USD)VRBO
From $230 per night (USD)VRBO
Escape to Paradise in Islamorada!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 11
Welcome to your perfect family-friendly getaway in the heart of Islamorada, Florida! Nestled between the sun-soaked shor ...
From $230 per night (USD)VRBO
From $592 per night (USD)VRBO
ISLAMORADA BEACH HOUSE
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Luxury Waterfront Home in Exclusive Port Antigua – Islamorada, FL Escape to this stunning 4,200 sq. ft. waterfront retr ...
From $592 per night (USD)VRBO
From $576 per night (USD)VRBO
Impressive Resort Like 5 Bedroom / 4.5 Baths with Pool & Dockage in Islamorada!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-ba ...
From $576 per night (USD)VRBO
From $234 per night (USD)VRBO
Spacious 3 bedroom home in Plantation key with 30 foot dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Make wonderful memories at this unique and family-friendly waterfront townhouse located on a deep-water canal with 30 fo ...
From $234 per night (USD)VRBO
From $866 per night (USD)Expedia
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Angler's Reef is located at MM85 in Islamorada, the heart of the Florida Keys. Our gated community is made up of 52 luxu ...
From $866 per night (USD)Expedia
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On the water in Islamorada elevated detached unit!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Topsider resort is a unique water front property where all the units are elevated and detached featuring 2 bedrooms & 2 ...
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From $551 per night (USD)Expedia
Islamorada retreat \"Bungalow Blue\" w/ heated pool, Bikes, BBQ, amenities galore!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to paradise! Completely remodeled and immaculately maintained... Bungalow Blue is nestled away in the quiet qua ...
From $551 per night (USD)Expedia
From $348 per night (USD)VRBO
Large Screened Porch, Professional Cleaning, Wifi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Oceanfront 90 mm Plantation Key , full screened in terrace 6.5 ft by 28.5 ft. Newly decorated white tile & Berber carp ...
From $348 per night (USD)VRBO
From $402 per night (USD)Expedia
Modern Cozy Beachouse Gem
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Elegant modern coastal gem! With beautiful canal views as well as incredible views of native area. Quiet, peaceful home ...
From $402 per night (USD)Expedia
From $293 per night (USD)VRBO
Large Keys Home in Heart of Tavernier with 50 ft of deep water dock.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Incredibly comfortable home located in the heart of Tavernier Key Mile Marker 90. Large home featuring incorporated do ...
From $293 per night (USD)VRBO
From $120 per night (USD)Expedia
Charming oceanfront condo with pool, beach access, tennis, & washer/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Escape to the Keys A6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $120 per night (USD)Expedia
From $588 per night (USD)VRBO
🌴 Oceanview Islamorada Penthouse 3BR 2 BA Sunrise Views, Pool & Weekly Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🌴 Welcome to Your Islamorada Escape 🌴 Keys Oceanview Penthouse – Weekly Rental in Islamorada Stay in one of the only ...
From $588 per night (USD)VRBO
From $173 per night (USD)VRBO
Home in Paradise- Tavernier Cottage,p Pool & Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Totally remodeled, canal front home, quiet and in the nicest neighborhoods (Plantation Key Colony). Situated on the bays ...
From $173 per night (USD)VRBO
From $976 per night (USD)VRBO
Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your private Islamorada oasis — an oceanfront 4-bed, 3-bath home with a newly renovated gourmet kitchen, brig ...
From $976 per night (USD)VRBO
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Tropical Vacation Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Quiet neighborhood located on a canal one block from the Atlantic Ocean. Home built in 2019, 2900 SF. Close to restauran ...
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From $626 per night (USD)VRBO
Island Time - Plantation Key Home with 4 beds & 3 baths with Pool & Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Island Time! This newly constructed canal front residence located in the heart of Plantation Key is sure to ...
From $626 per night (USD)VRBO
From $352 per night (USD)VRBO
Beautiful, Spacious, Single Story Home - Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This single-story canal front home located in the heart of Islamorada (MM86) in the Florida Keys-fishing capital of the ...
From $352 per night (USD)VRBO
From $277 per night (USD)VRBO
TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
New In Ground Heated pool , Just remodeled with new furniture, flat screen tvs throughout ( including the patio) and a d ...
From $277 per night (USD)VRBO
From $429 per night (USD)Expedia
Bungalow #4 - 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 $429 per night (USD)Expedia
From $529 per night (USD)VRBO
Fish Tail Palm Ocean View 1 Queen Bed, and 1 Pull Out
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ocean View 1 Queen Bed, and 1 Pull Out. Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, ...
From $529 per night (USD)VRBO
From $1622 per night (USD)Expedia
Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
King, Queen2 twins, 1 pullout. Boat Dockage Custom designed and built from the ground up by resort owner Phil Sena wit ...
From $1622 per night (USD)Expedia
From $189 per night (USD)VRBO
Spectacular Penthouse w/Panoramic Open Water Views-New rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Fantastic Penthouse Apartment is just steps away from the fabulous turquoise waters of Florida Bay! Enjoy spectacul ...
From $189 per night (USD)VRBO
From $199 per night (USD)Expedia
Eclectic Easeful Stay At The Keys!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come and enjoy this spacious, airy, and recently renovated condo at Summer Sea in beautiful Tavernier, Florida. The buil ...
From $199 per night (USD)Expedia
From $321 per night (USD)VRBO
Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to island time at beautiful Anglers Reef, the perfect way to experience and relax in the Florida Keys. Our hom ...
From $321 per night (USD)VRBO
From $295 per night (USD)VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free 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 $295 per night (USD)VRBO
From $736 per night (USD)VRBO
4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 4-bedroom, 3.5 bath home in Angler's Reef. Located at MM85, this tastefully decorated, open floor plan feature ...
From $736 per night (USD)VRBO
From $411 per night (USD)VRBO
Your Home Away From Home! Onsite Pool, Free Breakfast, 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 $411 per night (USD)VRBO
From $411 per night (USD)VRBO
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
- 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 $411 per night (USD)VRBO
From $411 per night (USD)VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
- 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 $411 per night (USD)VRBO
From $266 per night (USD)VRBO
Canal-Front Florida Keys Home w/ Dock!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Ocean breezes and beautiful water views are in store at this 2-bedroom, 2-bathroom home. This Florida Keys vacation rent ...
From $266 per night (USD)VRBO
From $329 per night (USD)VRBO
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $329 per night (USD)VRBO
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Pristine canal-front home with heated pool and access to open water
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Beautifully appointed getaway perfectly situated to allow exploration of the mangroves or the open water, since Tavernie ...
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Click For PricingExpedia
FLORIDA KEYS
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
ONLY WEEK AVAILABLE: OCTOBER 5-12, 2024. Caloosa Cove Resort and Marina is located on 10 tropical acres in Islamorada, F ...
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From $697 per night (USD)VRBO
Luxury Home with 60' Deep Water Dock, Waterfall Pool, HotTub, A/C and WiFi
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Minimum 28 day stay. Dreaming of a FL Keys vacation where you can boat, fish, dive, snorkel or stay home and swim in yo ...
From $697 per night (USD)VRBO
From $335 per night (USD)VRBO
Family Escape in Islamorada! Seaside Unit w/ Balcony! 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 $335 per night (USD)VRBO
From $356 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 $356 per night (USD)VRBO
From $263 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 $263 per night (USD)VRBO
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
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 $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 $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 $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 $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 $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 $558 per night (USD)Expedia
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)Expedia
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 $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 $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 $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 $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 $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 $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)Expedia
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)Expedia
From $199 per night (USD)VRBO
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)VRBO
From $897 per night (USD)Expedia
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)Expedia
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 $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 $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 $468 per night (USD)VRBO
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)VRBO
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)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 $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
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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 $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 $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)VRBO
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)VRBO
From $771 per night (USD)Expedia
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)Expedia
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
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