Holiday rentals with a pool in The Villages
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in The Villages
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 The Villages rentals with a pool
House rentals with a pool
Home in The Villages
4.91 out of 5 average rating, 23 reviewsBeautiful Designer Home in The Villages Fl
28 Jul – 4 Aug
Home in The Villages
4.98 out of 5 average rating, 50 reviewsLAVISH Private House w/ King Bed Suites, Remodeled
30 May – 6 Jun
Home in The Villages
5.0 out of 5 average rating, 19 reviewsHaven Escape at the Village of Richmond
15–22 Jul
Home in The Villages
4.95 out of 5 average rating, 75 reviews1199 Merryweather - Walk to Lake Sumter Landing Sq
12–19 Jun
Home in The Villages
4.95 out of 5 average rating, 55 reviews3 BR 2 BA Coastal-vibe Golf Cart, Pool, Pickleball
15–22 Nov
Home in Wildwood
4.93 out of 5 average rating, 29 reviewsJune Rates Reduced 2/2 in Village of Citrus Grove
4–11 Sep
Home in Lady Lake
4.94 out of 5 average rating, 18 reviewsRelaxing House in The Villages
7–14 Nov
Home in The Villages
4.91 out of 5 average rating, 34 reviewsSunny Daze Inn with Golf Cart!
23–30 May
Apartment rentals with a pool
Apartment in Inverness
4.89 out of 5 average rating, 35 reviewsCypress Cove Waterfront Townhome
16–23 Apr
Apartment in Inverness
5.0 out of 5 average rating, 18 reviewsGray Heron Victorian Townhouse
22–29 Nov
Apartment in Windermere
4.94 out of 5 average rating, 16 reviewsCozy Luxury2BR Apt/Resort Pool/Balcony/Close2Parks
14–21 Nov
Apartment in Windermere
5.0 out of 5 average rating, 15 reviewsLuXury Apt with Lake View, Cable & fast WiFi
9–16 Jul
Apartment in Apopka
Tranquil 2B/2B Stay in Apopka
27 Jun – 4 Jul
Apartment in Clermont
4.69 out of 5 average rating, 13 reviewsSunny Clermont Retreat ~ 20 Mi to Disney World!
24 Jun – 1 Jul
Apartment in Windermere
4.67 out of 5 average rating, 12 reviewsClassic Getaway to Windermere
29 Mar – 5 Apr
Apartment in Kissimmee
Beautiful 1 Bedroom Standard Villa Close To Disney
8–15 Sep
Home rentals with a private pool
Home in Inverness
Spacious Pool Home, Family & Golf Trips-4727
2–9 Oct
Home in Inverness
Gorgeous Vacation Home Ciska
25 Aug – 1 Sep
Home in Inverness
Beautiful & Sunny Pool Home with Golf View
5–12 Aug
Home in Inverness
Spacious Home with Private Pool & Jacuzzi
26 Sep – 3 Oct
Home in Inverness
Vacation Home with a Stunning View - 870
13–20 Sep
Home in Inverness
Family Villa Bettina - Recently Remodeled
12–19 Dec
Villa in Inverness
North Foxrun Terrace Villa 1512
27 Aug – 3 Sep
Home in Hernando
Four Bedroom Comfort Villa 4668
19–26 Sep
Quick stats about holiday rentals with a pool in The Villages
Total rentals
350 properties
Rentals with dedicated workspaces
200 properties have a dedicated workspace
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
310 properties are a good fit for families
Total number of reviews
6.4K reviews
Nightly prices starting at
€ 37 before taxes and fees
Destinations to explore
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Tampa Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- Naples Holiday rentals
- West Palm Beach Holiday rentals
- Boca Raton Holiday rentals
- Fort Lauderdale Holiday rentals
- Miami Beach Holiday rentals
- Miami Holiday rentals
- Charleston Holiday rentals
- Rentals with pools United States
- Rentals with pools Orlando
- Rentals with pools Florida
- Rentals with pools Florida
- Rentals with pools Kissimmee
- Waterfront rentals The Villages
- Rentals with a fireplace The Villages
- Rentals with a washing machine and dryer The Villages
- Rentals with a hot tub The Villages
- House rentals The Villages
- Rentals with breakfast The Villages
- Rentals with a patio The Villages
- Family-friendly rentals The Villages
- Pet-friendly rentals The Villages
- Rentals with lake access The Villages
- Rentals with outdoor seating The Villages
- Monthly Rentals The Villages
- Rentals with a firepit The Villages
- Villa rentals The Villages
- Family-friendly rentals The Villages
- Rentals with pools Marion 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