Islamorada Vacation Rentals
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Bathrooms
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5 mi
746 rentals in Islamorada.
Wonderful 2 Bedroom Condo with Ocean Views
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ULTIMATE outdoor living area at this 4/4 canal home with pool!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Southern Diversion Estate Islamorada Thanksgiving open deep discount
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Beautifully Renovated 2 Bedroom Condo
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Better Choice for your Vacation! 2 Pet-Friendly Units, Free Breakfast, Pool
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Prime Location! Onsite Pool, Free Breakfast, Free Parking
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!"
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Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock
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Paradise Retreat
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Islamorada Hidden Treasure
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Luxury Waterfront Condo with Boat Slip
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Waterfront Paradise with Free Dockage - Contact us to price your stay!!
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Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Free Parking
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Home on Canal with Private Beach Access / 4 bedroom 3 bath
Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Best Place to Unwind! 2 Spacious Units, Free Breakfast, Swimming Pool!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Updated Unit with Beautiful Florida Bay Sunsets
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
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Beautiful sunsets & water views
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bay front 6BDr Private Beach Pickle-ball Ct Game room Sunset Views
Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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10 Bedroom Private Ocean Front Estate
Rental Home
10 bedrooms
11 bathrooms
Sleeps 22
Match: Sleeps
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Come Create Memories w/ Fun-filled Adventures at this Paradise! Beachfront
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Port Antigua South Islamorada Canal Front Home with Pool Dock & Private Beach
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Isla Lychee: Little Basin Villas, Waterfront Boutique Resort, Walkable
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access
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Brand New Home, Resort Location, Ocean View
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! Breakfast
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Oceanside Resort... Oceanview unit with kayaks, paddleboards and walk in beach!
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Off the beaten path in one of Islamorada’s hidden gem of a community!.
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Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beachy 3 Bedroom Condo with Ocean Views
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Private Pool, Completely Renovated Lovely Cottage Home in Islamorada
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Your Majestic View in Islamorada! Swimming Pool, Kitchenette, Pets Allowed!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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This condo is located in one of Islamorada's most prestigious condo complexes.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Condo in Paradise!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Gated canal-front retreat with pool water access, grill, AC & 2 kitchens
Rental Home
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Florida Keys Chic
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Islamorada Island Getaway
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Modern ground-floor apartment with pool, water views, patio, grill, & central AC
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Isla Sunset Collection: Sleeps 18, All Ensuite Bedrooms, Waterfront
Rental Home
9 bedrooms
12 bathrooms
Sleeps 18
Match: Sleeps
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Water-view house with private dock, washer/dryer & grill - snowbird-friendly
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Luxury Home with 60' Deep Water Dock, Waterfall Pool, HotTub, A/C and WiFi
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4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
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Relaxation at its Finest in Islamorada! Swimming Pool, Beach, Pet-friendly!
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Premium Units w/ Ocean Views & Balcony! Marina, Pets Allowed, Beach Access!
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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This studio makes the best of the space
Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Showing results 1-50 of 746
Frequently Asked Questions about Islamorada
- 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!
- 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
- 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
- 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
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