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Vacation Rentals and House Rentals in Islamorada, FL
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Florida (FL)
Florida Keys
Islamorada Vacation Rentals
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Internet or Wifi (733)
Air Conditioning (728)
Grill (531)
Washer/Dryer (519)
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Suitability
Kid friendly (719)
Pet friendly (281)
Smoking allowed (24)
Elder access (6)
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Property type
Vacation Rental House (646)
Condominium/Apartment (100)
Cabin Vacation Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (426)
Boat Available (81)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
History of Diving Museum
Florida Keys Brewing Company
Alligator Reef Light House
Islamorada Brewery & Distillery - MM82
Windley Key Fossil Reef Geological State Park
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746 rentals
in Islamorada.
Wonderful 2 Bedroom Condo with Ocean Views
3
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 4
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ULTIMATE outdoor living area at this 4/4 canal home with pool!
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 10
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Southern Diversion Estate Islamorada Thanksgiving open deep discount
11
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 16
Match:
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Beautifully Renovated 2 Bedroom Condo
6
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 4
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Better Choice for your Vacation! 2 Pet-Friendly Units, Free Breakfast, Pool
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 8
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Prime Location! Onsite Pool, Free Breakfast, Free Parking
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
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"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!"
10
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 12
Match:
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Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock
52
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
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Paradise Retreat
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 8
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Islamorada Hidden Treasure
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
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Islamorada Luxury Waterfront Condo with Boat Slip
12
Condo/Apartment
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2 bedrooms
3 bathrooms
Sleeps 6
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Waterfront Paradise with Free Dockage - Contact us to price your stay!!
10
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
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Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
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Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Free Parking
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
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Islamorada Home on Canal with Private Beach Access / 4 bedroom 3 bath
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 11
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Best Place to Unwind! 2 Spacious Units, Free Breakfast, Swimming Pool!
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 8
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Updated Unit with Beautiful Florida Bay Sunsets
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 3
Match:
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Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
23
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
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Beautiful sunsets & water views
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
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Bay front 6BDr Private Beach Pickle-ball Ct Game room Sunset Views
Rental Home
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6 bedrooms
4 bathrooms
Sleeps 12
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10 Bedroom Private Ocean Front Estate
Rental Home
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10 bedrooms
11 bathrooms
Sleeps 22
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Come Create Memories w/ Fun-filled Adventures at this Paradise! Beachfront
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
Match:
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Port Antigua South Islamorada Canal Front Home with Pool Dock & Private Beach
5
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
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Isla Lychee: Little Basin Villas, Waterfront Boutique Resort, Walkable
Rental Home
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
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Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
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Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
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Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access
10
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 4
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Brand New Home, Resort Location, Ocean View
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
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Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! Breakfast
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
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Oceanside Resort... Oceanview unit with kayaks, paddleboards and walk in beach!
10
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
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Off the beaten path in one of Islamorada’s hidden gem of a community!.
4
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
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Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property
Rental Home
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1 bedroom
1 bathroom
Sleeps 3
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Beachy 3 Bedroom Condo with Ocean Views
5
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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Private Pool, Completely Renovated Lovely Cottage Home in Islamorada
10
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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Your Majestic View in Islamorada! Swimming Pool, Kitchenette, Pets Allowed!
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 8
Match:
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This condo is located in one of Islamorada's most prestigious condo complexes.
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Charming Condo in Paradise!
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Gated canal-front retreat with pool water access, grill, AC & 2 kitchens
Rental Home
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6 bedrooms
4 bathrooms
Sleeps 10
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Florida Keys Chic
2
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Islamorada Island Getaway
10
Rental Home
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5 bedrooms
5 bathrooms
Sleeps 8
Match:
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Modern ground-floor apartment with pool, water views, patio, grill, & central AC
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
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Isla Sunset Collection: Sleeps 18, All Ensuite Bedrooms, Waterfront
Rental Home
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9 bedrooms
12 bathrooms
Sleeps 18
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Water-view house with private dock, washer/dryer & grill - snowbird-friendly
1
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
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Luxury Home with 60' Deep Water Dock, Waterfall Pool, HotTub, A/C and WiFi
8
Rental Home
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5 bedrooms
5 bathrooms
Sleeps 14
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4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
25
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 8
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Relaxation at its Finest in Islamorada! Swimming Pool, Beach, Pet-friendly!
Rental Home
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2 bedrooms
1 bathroom
Sleeps 6
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Premium Units w/ Ocean Views & Balcony! Marina, Pets Allowed, Beach Access!
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
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Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument
Rental Home
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1 bedroom
1 bathroom
Sleeps 2
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Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
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This studio makes the best of the space
Rental Home
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2 bedrooms
1 bathroom
Sleeps 2
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Showing results 1-50 of 746
Frequently Asked Questions about Islamorada
Do any vacation rentals in Islamorada have a pool?
Yes, here are some popular vacation rentals in Islamorada that have a pool:
Ocean Front Town House With Breath Taking Views From all 3 Balconies
Wonderful 2 Bedroom Condo with Ocean Views
ULTIMATE outdoor living area at this 4/4 canal home with pool!
See all vacation rentals with a pool in Islamorada on Tripadvisor
Do any vacation rentals in Islamorada have internet access?
Yes, here are some popular vacation rentals in Islamorada that have internet access:
Wonderful 2 Bedroom Condo with Ocean Views
ULTIMATE outdoor living area at this 4/4 canal home with pool!
Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside
See all vacation rentals in Islamorada on Tripadvisor
What are the best pet friendly rentals in Islamorada?
The best pet friendly rentals in Islamorada are:
ULTIMATE outdoor living area at this 4/4 canal home with pool!
Pets are Allowed Here! 2 Comfortable Units, Free Breakfast, Parking, Pool
Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock
See all pet friendly vacation rentals in Islamorada on Tripadvisor
What are some great rentals in Islamorada that are kid friendly?
Some of the most popular kid friendly rentals in Islamorada are:
Wonderful 2 Bedroom Condo with Ocean Views
ULTIMATE outdoor living area at this 4/4 canal home with pool!
Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside
See all kid friendly vacation rentals in Islamorada on Tripadvisor
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