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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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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
Match:
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Modern Oceanview Paradise at Islamorada
2
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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You will love my "Fl Keys Luxury Home"
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 10
Match:
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4BR waterfront home with POOL, boat slip with straight shot to Alligator Reef!
1
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 10
Match:
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Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
1
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Beautiful 'Keysey' Condo in Bay Harbour Gated Community 24-0169
1
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 4
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The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip
15
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
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Tropical Paradise
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
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Oceanfront, Private Pool Oasis!
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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Incredible Bayside Home in the Florida Keys!
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
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ISLAMORADA BEACH HOUSE
1
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
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4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 16
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Indulge in Home Like Comfort! Courtyard View, Free Parking, Pool, Pets Allowed
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
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Private 2 Acre Bayside Waterfront Estate 2/2 All To Yourself ~ New Listing!
2
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
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Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 15
Match:
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Exec Bay 3 Bedroom townhouse w/heated pool, marina, tennis & more
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
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Oceanfront Estate in the Heart of Islamorada
1
Rental Home
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5 bedrooms
6 bathrooms
Sleeps 10
Match:
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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay
10
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
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Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Private Tropical Oasis
4
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Relax in this updated townhome while overlooking the sparkling Atlantic Ocean
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Beautiful Studio Apartment - Summer Sea Condo #230
1
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
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3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 12
Match:
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Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK
10
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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Coastal Retreat ~ Brand New 4-Bedroom Home in the Heart of Islamorada
Rental Home
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4 bedrooms
5 bathrooms
Sleeps 8
Match:
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Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
17
Condo/Apartment
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2 bedrooms
3 bathrooms
Sleeps 4
Match:
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Ocean Harbor Paradise in Islamorada
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
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Dive Into Your Dream Vacation! 3 Spacious Units, Onsite Pool, FREE Breakfast!
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 12
Match:
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Ocean Front Villa, 3/4's acre of private beach! Serenity, Retreat, Island Life!
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 14
Match:
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Cozy Coastal Haven for Relaxation! With Pools and Water Sports Onsite!
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
Match:
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2 Spacious Garden Suite w/ Kitchenette | Outdoor Pool + Beach Access
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 12
Match:
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Romantic Studio Cottage Nestled in Lush Landscaping with Pool and Dockage
10
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Florida Keys' Jewel - Executive Bay Club
7
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
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Steps Away from Coral Bay Marina! Pool, Beachfront, Free Parking, Pets Allowed
Rental Home
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun
49
Rental Home
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
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Malayan Palm North 2 Bedrooms, 1 Bath, Garden View
1
Rental Home
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Islamorada Keys Home In Anglers Reef With Ocean View, Dock, Pool & Beach
194
Rental Home
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2 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
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Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
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Beach Dream House, relax and enjoy the clear waters of Islamorada FL
55
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Executive Bay Club Bayfront/Beachfront paradise
1
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Relax and Unwind Near Robbie's of Islamorada! FREE Parking & Breakfast, Pool!
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
Match:
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Harbor house 2 Bedrooms, 2 Baths, Partial Ocean View
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
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Princess Palm South Poolside,1 King Bed, 2 FullBeds, 1 Pull Out
Rental Home
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2 bedrooms
1 bathroom
Sleeps 8
Match:
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Venetian Shores 5bed 7b, Pool , Spa, Boat lifts, open for Oct 2024
Rental Home
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5 bedrooms
8 bathrooms
Sleeps 10
Match:
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Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
Match:
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Charming 2 Bedroom Ground Level Home with Bay Views
4
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock
64
Rental Home
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5 bedrooms
5 bathrooms
Sleeps 10
Match:
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Malayan Palm East 1 Bedroom, 1 Bath Garden View
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Fantastic ocean front conch house on the ocean with 160’ dock.
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 4
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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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