Vacation rentals with a pool in Florida Keys
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Florida Keys
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Florida Keys rentals with a pool
House rentals with a pool
Home in Key Colony Beach
4.81 out of 5 average rating, 132 reviewsWaterview from three sides, Cabana Club, 30' Docks
Aug 3 – 10
Home in Marathon
5.0 out of 5 average rating, 16 reviewsHorizon
Aug 31 – Sep 7
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
Feb 27 – Mar 6
Home in Marathon
4.97 out of 5 average rating, 33 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Dec 14 – 21
Home in Upper Sugarloaf Key
4.87 out of 5 average rating, 45 reviewsBungalows at Sugarloaf Beach - The Lighthouse
Sep 23 – 30
Home in Marathon
4.97 out of 5 average rating, 36 reviewsWaterfront Private Home w/Pool-Family&Pet Friendly
Oct 6 – 13
Home in Key Colony Beach
5.0 out of 5 average rating, 65 reviews“La casa azul” step 3’ to a private pool
Nov 2 – 9
Home in Duck Key
5.0 out of 5 average rating, 31 reviewsPrivate Pool Tropical Oasis - Centrally Located
Nov 20 – 27
Condo rentals with a pool
Condo in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Aug 25 – Sep 1
Condo in Tavernier
4.93 out of 5 average rating, 134 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
Jul 12 – 19
Condo in Tavernier
4.99 out of 5 average rating, 101 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
Aug 24 – 31
Condo in North Bay Village
4.86 out of 5 average rating, 237 reviewsGorgeous studio with water & downtown view.
Aug 27 – Sep 3
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Aug 22 – 29
Condo in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Apr 25 – May 2
Condo in Tavernier
4.88 out of 5 average rating, 229 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Sep 26 – Oct 3
Condo in Tavernier
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
Sep 2 – 9
Home rentals with a private pool
Home in Marco Island
4.83 out of 5 average rating, 6 reviewsLighthouse 1124
Apr 19 – 26
Home in Fort Lauderdale
4.63 out of 5 average rating, 32 reviewsMid Century Modern Pool Home In the Best Location!
Oct 22 – 29
Home in Wilton Manors
4.64 out of 5 average rating, 14 reviewsTowering Palms, Wilton Manors - Heated Pool & Spa
Aug 19 – 26
Home in Marco Island
4.83 out of 5 average rating, 6 reviewsSandcastle of Marco Island Waterfront Private Pool
Mar 5 – 12
Home in Fort Lauderdale
Luxurious Oasis In Fort Lauderdale's Heart
Aug 1 – 8
Home in Wilton Manors
4.43 out of 5 average rating, 7 reviewsShangri-La
Nov 4 – 11
Condo in Hollywood
Resort Condo Stunning White Sand Beaches
Nov 2 – 9
Home in Fort Lauderdale
A Snow Fort Iii - Poinsettia Heights Gem
Feb 8 – 15
Destinations to explore
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- Key West Vacation rentals
- Naples Vacation rentals
- West Palm Beach Vacation rentals
- Varadero Vacation rentals
- Havana Vacation rentals
- Nassau Vacation rentals
- Sarasota Vacation rentals
- Anna Maria Island Vacation rentals
- Rentals with pools Miami
- Rentals with pools United States
- Rentals with pools Miami Beach
- Rentals with pools Florida
- Rentals with pools Fort Lauderdale
- House rentals Florida Keys
- Rentals with outdoor seating Florida Keys
- Monthly Rentals Florida Keys
- Rentals with a kayak Florida Keys
- Bed and breakfasts Florida Keys
- Rentals with a fireplace Florida Keys
- Waterfront rentals Florida Keys
- Boutique hotel rentals Florida Keys
- Private suite rentals Florida Keys
- Beach house rentals Florida Keys
- Hotel rentals Florida Keys
- Bungalow rentals Florida Keys
- Rentals with a sauna Florida Keys
- Rentals with a patio Florida Keys
- Apartment rentals Florida Keys
- Townhouse rentals Florida Keys
- RV rentals Florida Keys
- Tiny house rentals Florida Keys
- Campsite rentals Florida Keys
- Rentals with an EV charger Florida Keys
- Rentals with a fire pit Florida Keys
- Fitness-friendly rentals Florida Keys
- Serviced apartment rentals Florida Keys
- Rentals with beach access Florida Keys
- Boat rentals Florida Keys
- Rentals with a hot tub Florida Keys
- Rentals with breakfast Florida Keys
- Rentals with an accessible height toilet Florida Keys
- Smoking-friendly rentals Florida Keys
- Rentals with a washer and dryer Florida Keys
- Beachfront rentals Florida Keys
- Villa rentals Florida Keys
- Mansion rentals Florida Keys
- Rentals with a home theater Florida Keys
- Rentals with lake access Florida Keys
- Rentals with an accessible height bed Florida Keys
- Kid-friendly rentals Florida Keys
- Condo rentals Florida Keys
- Resort rentals Florida Keys
- Houseboat rentals Florida Keys
- Family-friendly rentals Florida Keys
- Wheelchair accessible rentals Florida Keys
- Pet-friendly rentals Florida Keys
- Guesthouse rentals Florida Keys
- Cottage rentals Florida Keys
- Beach condo rentals Florida Keys
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes