
Holiday rentals with a pool in Islamorada
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Islamorada
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Islamorada rentals with a pool
House rentals with a pool

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

Waterfront Escape -VACA-23-408

Paradise found!Key Colony Beach,Cabana Club.

Cancellation Deal: 08/02 thru 08/09

4BR 3B, Heated Pool & Spa, 60' Dock

Oceanfront with Pool near Sombrero Beach

Waterfront Home 37.5-ft dock, Cabana Club Included

Newely Renovated 3/2-private pool/dock/cabana club
Condo rentals with a pool

Reel Large END Unit in Ocean Point Suites

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Your Happy Place - Oceanfront

2BR - Key Largo Sunshine Getaway

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Ocean Views at Ocean Pointe

Tropical Getaway

Sugar Cane - Florida Keys tropical retreat
Quick stats about holiday rentals with a pool in Islamorada
Total rentals
610 properties
Nightly prices starting at
$115 NZD before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
420 properties are a good fit for families
Pet-friendly rentals
260 properties allow pets
Rentals with dedicated workspaces
340 properties have a dedicated workspace
Destinations to explore
- Florida Keys Holiday rentals
- Miami Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Key West Holiday rentals
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Bay Holiday rentals
- Central Florida Holiday rentals
- St Petersburg Holiday rentals
- Kissimmee Holiday rentals
- Tampa Holiday rentals
- Rentals with beach access Islamorada
- Luxury rentals Islamorada
- Rentals with a hot tub Islamorada
- Rentals with a washing machine and dryer Islamorada
- Condo rentals Islamorada
- Townhouse rentals Islamorada
- Bungalow rentals Islamorada
- Beach house rentals Islamorada
- House rentals Islamorada
- Rentals with a fire pit Islamorada
- Rentals with outdoor seating Islamorada
- Apartment rentals Islamorada
- Rentals with an EV charger Islamorada
- Beachfront rentals Islamorada
- Rentals with a kayak Islamorada
- Pet-friendly rentals Islamorada
- Kid-friendly rentals Islamorada
- Fitness-friendly rentals Islamorada
- Waterfront rentals Islamorada
- Villa rentals Islamorada
- Rentals with a fireplace Islamorada
- Family-friendly rentals Islamorada
- Rentals with a patio Islamorada
- Rentals with breakfast Islamorada
- Rentals with pools Monroe County
- Rentals with pools Florida
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Bahia Honda State Park
- Coral Castle
- Biscayne National Park
- Cannon Beach
- Conch Key
- Calusa Beach & Loggerhead Beach
- Everglades Alligator Farm
- Theater of the Sea
- Long Beach
- Cocoa Plum Beach
- EAA Air Museum
- Monkey Jungle
- Far Beach
- Horseshoe Beach
- Windley Key Fossil Reef Geological State Park
- Long Key State Park
- Keys' Meads