Accommodation with a pool in Monroe County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Monroe County
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 Monroe County rentals with a pool
House rentals with a pool
Home in Cudjoe Key
4.97 out of 5 average rating, 122 reviewsCudjoe Key Home with a View
29 Aug – 5 Sept
Home in Marathon
4.99 out of 5 average rating, 107 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
24 – 31 Aug
Home in Miami
5.0 out of 5 average rating, 238 reviewsModern,spacious Retreat !Salt water,heated pool!
24 Sept – 1 Oct
Home in Cudjoe Key
4.9 out of 5 average rating, 104 reviewsSunrise Beach Escape
14 – 21 Apr
Home in Homestead
4.93 out of 5 average rating, 358 reviewsPrivate Paradise between Miami & the Keys
29 Apr – 6 May
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
27 Feb – 6 Mar
Home in Upper Sugarloaf Key
4.87 out of 5 average rating, 45 reviewsBungalows at Sugarloaf Beach - The Lighthouse
23 – 30 Sept
Home in Marathon
4.97 out of 5 average rating, 33 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
14 – 21 Dec
Condo rentals with a pool
Condo in Key Colony Beach
4.96 out of 5 average rating, 171 reviewsOceanfront Sunrise Condo Private Beach Heated Pool
13 – 20 Nov
Condo in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
25 Aug – 1 Sept
Condo in Key West
4.93 out of 5 average rating, 132 reviewsBeach Club Ocean Front 2BR Condo
5 – 12 Apr
Condo in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
25 Apr – 2 May
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
22 – 29 Aug
Condo in Tavernier
4.99 out of 5 average rating, 102 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
24 – 31 Aug
Condo in Tavernier
4.93 out of 5 average rating, 134 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
12 – 19 July
Condo in Key West
4.86 out of 5 average rating, 129 reviewsA Perfect Getaway
26 May – 2 June
Destinations to explore
- 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 Monroe County
- Apartment rentals Monroe County
- Private suite rentals Monroe County
- Farmstay rentals Monroe County
- Boat rentals Monroe County
- Serviced apartment rentals Monroe County
- Tiny house rentals Monroe County
- Rentals with a fire pit Monroe County
- Pet-friendly rentals Monroe County
- Smoking-friendly rentals Monroe County
- Rentals with an accessible height bed Monroe County
- Rentals with a sauna Monroe County
- Rentals with a home theatre Monroe County
- Campsite rentals Monroe County
- Hotel rentals Monroe County
- Ski-in/ski-out rentals Monroe County
- Loft rentals Monroe County
- Fitness-friendly rentals Monroe County
- Waterfront rentals Monroe County
- Beachfront rentals Monroe County
- Rentals with a fireplace Monroe County
- Bed and breakfasts Monroe County
- Rentals with outdoor seating Monroe County
- Rentals with lake access Monroe County
- Rentals with beach access Monroe County
- Luxury rentals Monroe County
- Monthly Rentals Monroe County
- Rentals with a hot tub Monroe County
- Rentals with an accessible height toilet Monroe County
- Villa rentals Monroe County
- RV rentals Monroe County
- Cottage rentals Monroe County
- Family-friendly rentals Monroe County
- Rentals with a kayak Monroe County
- Houseboat rentals Monroe County
- Townhouse rentals Monroe County
- House rentals Monroe County
- Rentals with an EV charger Monroe County
- Rentals with a washing machine and dryer Monroe County
- Rentals with a patio Monroe County
- Wheelchair accessible rentals Monroe County
- Kid-friendly rentals Monroe County
- Condo rentals Monroe County
- Guesthouse rentals 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