
Vacation rentals with a pool in The Villages
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in The Villages

Total vacation rentals
Explore 330 vacation rentals in The Villages

Nightly prices starting at
The Villages vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

Verified guest reviews
Over 8,210 verified reviews to help you choose

Family-friendly vacation rentals
290 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 120 rentals that welcome pets

Rentals with dedicated workspaces
200 properties have a dedicated workspace

Wi-Fi availability
330 of The Villages vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across The Villages rentals

4.9 Average rating
The Villages stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in The Villages
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

2/2 custom pool home with 4 person gas golf cart
Beautiful Monterey style 1600 SQFT home, 2BR/2BA, fully furnished with a heated pool at 85' year round. Great location in Rio Grande; just a short golf cart ride to Spanish Springs & Lake Sumter. Home is on a quiet cul-de-sac; no neighbors behind. Private lanai from the Florida room. Tile and granite countertops throughout; Stainless steel appliances; sleeper sofa in the LR. 4 person gas golf cart also included. Sorry, hot tub not included. Dog friendly! Smart Tvs in both BRs, cable in LR only

Entire 3 BR Home(Sleeps 8)+Hot Tub in The Villages
Live Music on the Square. Golf , Pools, tennis, etc Spacious 3 bedroom house in The Villages. The house has a hot tub on the back lanai. The house is newly renovated and features both a new 70 inch Samsung TV in the living room and a new 50 inch Samsung TV in the master bedroom with Hulu Live and Comcast Business high speed internet. The house is located near the Spanish Springs Town Center and Glenview Country Clubs. The home sleeps 8 with privacy using a sofa bed located in the rec room.

Pool House Near Eastport and Middleton
Relax at this peaceful new home in The Villages. Only minutes to Eastport, Sawgrass and Middleton. Enjoy the beautiful outdoor area and heated pool (heated for additional $20/day) with plenty of space and seating. There are TVs in the living bedrooms and the lanai to watch from the pool or comfortable outdoor seating. There’s a king bed in the master and queens in each of the guest bedrooms. Your stay includes a gas 4-seater Yamaha golf cart and probably a 2nd cart. That one’s not promised.

Sunset Oasis - 3/2 w/ Pool & Golf Cart
Breathtaking! This 3BR 2BA w/ POOL and GOLF CART, in the Village of Lake Denham, will leave you speechless! Not only is paradise inside the house, but you have an amazing waterfront view while you revel in the private pool. Comfortable beds, open floor plan, it's stunning! Cruise around on the golf cart to discover rec. centers, pools, golf courses for all level of players, and pickleball courts. The squares certainly won't disappoint with their restaurants, shopping and nightly live music.

Casa Santin Luxury in The Villages w/Private Pool
A refined Florida Luxury home designed for effortless indoor-outdoor living, Casa Santin blends modern coastal style with relaxed comfort—creating the perfect escape for your next getaway. Your Private Oasis. The highlight of Casa Santin is the stunning screened lanai and private pool—your own resort-style sanctuary. Start your mornings with coffee in the sunshine, spend afternoons poolside, and unwind in the evenings with a western sunset, a glass of wine under the soft glow of the lanai.

New Luxury Home-Pool-Waterfront View-3 King Suites
Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

Location Can’t be Beat! With cart!
Experience The Village's retirement community lifestyle! The patio villa is located near Spanish Springs Town Square and the shopping corridor, where you will find nightly entertainment, dining and shopping. Walk to Savannah Center & Glenview Country Club. Your rental includes the complimentary use of a Yamaha gas golf cart and Guest ID cards that provide you access to our recreation facilities. Monthly guests may purchase Resident ID cards ($50) that include free executive golf.

Fabulous Courtyard Villa close to Sumter Landing
This home is the perfect vacation. When we saw this beautifully decorated villa, we felt like we were home. The exquisite landscaping was exactly what we have been looking for! The location is a mile from Sumter Landing and a stone's throw from the two pools, billiards, shuffleboard, pickleball, bocce ball. The best way to see it all is by the golf cart!!! The Villages has its own GPS for the Cart Paths. Schedule your stay and start packing your bags for an amazing experience.

King Bed, Golf Cart, Small Dogs & Water Filter!
Your NEW home includes a very comfortable KING BED and GOLF CART!! With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house NOVA WATER filtration system, you’ll have everything you need for a relaxing and enjoyable stay in The Villages. Find out why The Villages is the fastest growing and largest 55+ community in the WORLD, where visitors of all ages are welcome to play. The fun and sun is only the beginning!! 2 SMALL DOGS OK.

Briar Meadow Villa - Dogs are welcome!
Dogs are welcome in this nicely furnished Courtyard Villa, with a fenced in backyard. Near Nancy Lopez Legacy Golf & Country Club, Mulberry Grove Rec Center, dog park, Publix, Walgreens, & The Club Health & Rehab Clinic. Easy access to pools, golf courses, dining, shopping & the squares at Spanish Springs & Sumter Landing. Includes gas Golf Cart*, Comcast cable TV, high speed WIFI, & Villages Daily Sun. *Subject to availability

Villages-Private Heated Pool-Central Location
Enjoy a stylish experience at this centrally located 3-bedroom home. 5-7 minutes golf cart ride from Sumter Landing, 15 minutes from Spanish Springs Square, 20 minutes from Brownsville Square. 200 Community pools some for adults only and some for families. 13 Recreation Centers with Pickle Ball, Shuffleboard, Billiards, Study groups, etc. 3 Old Fashion Town Squares with nightly Live entertainment. 44 Golf Courses

Stylish Villages Getaway
Welcome to your modern luxury escape in The Villages. Perfect for snowbirds, couples, or families, this brand-new home is designed for comfort and convenience. Enjoy high-end furnishings, elegant interiors, and access to resort-style community amenities. Make the most of your stay with a premium 6-passenger golf cart, electric bikes, and endless entertainment. Stay active, relax, and create unforgettable memories.
Popular amenities for The Villages rentals with a pool
House rentals with a pool

Pirates & Parrots - The Villages - Golf Cart &Pool

The Grandview

House on Golf Course, with Heated Pool & Golf Cart

New, private pool getaway in The Villages, FL

The Palms. Luxurious, giant pool, golf, pond view

The Creative Cottage! Premium Amenities!

Eastport Emerald Escape 2BR Luxury in Well Point

The Villages-3 bd (3 king)/3 full ba+Cart NEW HOME
Other vacation rentals with a pool

Perfect location Lake Sumpter Villa w/ Golf Cart

Heated Pool Golf Cart Dog Friendly in The Villages

The Eastport Escape | New 3BR | King + Golf Cart

Living the Dream | Pools, Golf & Entertainment

Designer Home in The Villages, FL.

Spotless 3BR Home w/ Golf Cart, Near Brownwood Sq

Charming Villages Retreat

StJohns is a great area for golf, hiking, Kayaking
When is the best time to visit The Villages?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 654 | ﺩ.ﺇ 716 | ﺩ.ﺇ 727 | ﺩ.ﺇ 474 | ﺩ.ﺇ 452 | ﺩ.ﺇ 433 | ﺩ.ﺇ 386 | ﺩ.ﺇ 375 | ﺩ.ﺇ 422 | ﺩ.ﺇ 433 | ﺩ.ﺇ 499 | ﺩ.ﺇ 521 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Destinations to explore
- Miami Vacation rentals
- Four Corners Vacation rentals
- Miami Beach Vacation rentals
- Orlando Vacation rentals
- Fort Lauderdale Vacation rentals
- Panama City Beach Vacation rentals
- Tampa Vacation rentals
- Destin Vacation rentals
- Hollywood Vacation rentals
- Savannah Vacation rentals
- Charleston Vacation rentals
- Jacksonville Vacation rentals
- Villa rentals The Villages
- Rentals with a hot tub The Villages
- Rentals with a washer and dryer The Villages
- House rentals The Villages
- Rentals with a fireplace The Villages
- Apartment rentals The Villages
- Pet-friendly rentals The Villages
- Rentals with lake access The Villages
- Waterfront rentals The Villages
- Rentals with a patio The Villages
- Family-friendly rentals The Villages
- Rentals with a fire pit The Villages
- Rentals with breakfast The Villages
- Cottage rentals The Villages
- Rentals with outdoor seating The Villages
- Rentals with pools Marion County
- Rentals with pools Florida
- Rentals with pools United States
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Weeki Wachee Springs
- Disney Springs
- SeaWorld Orlando
- Magic Kingdom Park
- Universal's Volcano Bay
- Epcot
- Camping World Stadium
- Rainbow Springs State Park
- Kia Center
- Disney's Animal Kingdom Theme Park
- Discovery Cove
- Tinker Field
- ESPN Wide World of Sports
- Disney's Hollywood Studios
- ICON Park
- Aquatica
- Island H2O Live!
- Epperson Lagoon
- Universal's Islands of Adventure
- Weeki Wachee Springs State Park





