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
Home in Marathon
4.97 out of 5 average rating, 118 reviewsMarathon one-level home on the Marina - with slip!
3–10 Dec
Home in Key Largo
4.97 out of 5 average rating, 108 reviewsTiny Home on Waterfront | Bay Views | Deck | Pool
13–20 Feb
Home in Key Largo
4.88 out of 5 average rating, 164 reviewsOutdoor Paradise - Beach, Boats, Snorkeling & Sun!
4–11 Jul
Home in Key Largo
4.9 out of 5 average rating, 127 reviewsBlue House Marine in Key Largo
9–16 Oct
Home in Islamorada
4.94 out of 5 average rating, 18 reviews3 Lux Ensuites Walk/Boat Island!
22–29 Mar
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
11–18 Aug
Home in Islamorada
5.0 out of 5 average rating, 12 reviewsAngler's Reef Gem in Islamorada!
25 Jan – 1 Feb
Home in Marathon
5.0 out of 5 average rating, 16 reviewsHorizon
31 Aug – 7 Sep
Apartment rentals with a pool
Apartment in Tavernier
4.99 out of 5 average rating, 101 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
8–15 Feb
Apartment in Tavernier
4.91 out of 5 average rating, 111 reviews500 Burton Drive Tavernier, Key Largo
15–22 Dec
Apartment in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
22–29 Aug
Apartment in Tavernier
4.87 out of 5 average rating, 126 reviewsReel Large END Unit in Ocean Point Suites
4–11 Oct
Apartment in Key Largo
4.98 out of 5 average rating, 115 reviewsOceanfront Condo w/Lake, Kayak, Paddleboard & Bike
7–14 Nov
Apartment in Tavernier
4.88 out of 5 average rating, 135 reviewsSpectacular 2 Bedroom with a beautiful ocean view.
23–30 Mar
Apartment in Tavernier
4.88 out of 5 average rating, 138 reviews2BR - Keys Paradise Getaway
26 Feb – 5 Mar
Apartment in Key Largo
4.97 out of 5 average rating, 147 reviewsKEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!
23–30 Apr
Quick stats about holiday rentals with a pool in Islamorada
Total rentals
640 properties
Rentals with dedicated workspaces
430 properties have a dedicated workspace
Pet-friendly rentals
330 properties allow pets
Family-friendly rentals
440 properties are a good fit for families
Total number of reviews
2.4T reviews
Nightly prices starting at
₹5,837 before taxes and fees
Destinations to explore
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Key West Holiday rentals
- Fort Lauderdale Holiday rentals
- Boca Raton Holiday rentals
- Naples Holiday rentals
- Varadero Holiday rentals
- West Palm Beach Holiday rentals
- Havana Holiday rentals
- Sarasota Holiday rentals
- Nassau Holiday rentals
- Anna Maria Island Holiday rentals
- Rentals with pools Miami
- Rentals with pools United States
- Rentals with pools Miami Beach
- Rentals with pools Florida
- Rentals with pools Fort Lauderdale
- Rentals with breakfast Islamorada
- Monthly Rentals Islamorada
- Family-friendly rentals Islamorada
- Pet-friendly rentals Islamorada
- Cottage rentals Islamorada
- Rentals with outdoor seating Islamorada
- Beach house rentals Islamorada
- Townhouse rentals Islamorada
- Beachfront rentals Islamorada
- Rentals with a fireplace Islamorada
- Flat rentals Islamorada
- Rentals with a washing machine and dryer Islamorada
- Family-friendly rentals Islamorada
- Rentals with a hot tub Islamorada
- Fitness-friendly rentals Islamorada
- Waterfront rentals Islamorada
- House rentals Islamorada
- Villa rentals Islamorada
- Apartment rentals Islamorada
- Rentals with a kayak Islamorada
- Rentals with a patio Islamorada
- Rentals with beach access Islamorada
- Rentals with a firepit Islamorada
- Rentals with pools Monroe County
- 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