
Vacation rentals with a pool in The Villages
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Top-rated rentals with a pool in The Villages
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

5-Star Luxury | Prime Location & Top Amenities
WITH GOLF CART IN THE VILLAGES TOTALLY REMODELED NO PETS in the heart of The Villages 2 bedrooms ,2-baths 2, TVS Every inch of this home has been updated with luxury vinyl plank flooring, and a fully equipped high-end kitchen with quartz countertops new cabinets, new stainless NEW steel appliances bedrooms newly renovated a king-size bed second bedroom a queen-size bed. 2 bathrooms completely renovated just minutes from Lake Sumter Landing and Spanish Springs Town Square ,entertainment,

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

Charming Villages Retreat
Charming 2B/2B Cottage Villa near Sumter Landing and Spanish Springs Escape to this beautifully updated villa in The Villages. Enjoy a designer kitchen, cozy living room with sectional and 75” TV, and French doors leading to a screened lanai. The private, fenced courtyard is perfect for relaxing under party lights. The master suite includes a walk-in closet and blackout shades. Explore with the included golf cart, access 50 golf courses, 100+ pickleball courts, pools, and nightly entertainment.

Cozy Lady Lake Guest House
Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

Robin's Song in Brownwood
WELCOME to the beautiful ROBIN's SONG conveniently located in The Village of Atwood where you are just minutes from all the fun and activities in The Villages. Just a 2 minute ride on the Yamaha GOLF CART (extra charge) into the famous BROWNWOOD PADDOCK SQUARE where you will enjoying shopping, dinning and live music each evening from 5 to 9 p.m. Just a minute ride to THE GRAND TRAVERSE PLAZA housing Publix, or the relaxing Brownwood Hotel and Day spa featuring the Wolfgang Puck Restaurant.

King-Sized Comfort
Take a break and unwind at this peaceful oasis.Welcome to your serene getaway in The Villages! This spacious “Hideaway” in peaceful DeLuna offers 2 king beds, 2 baths, and easy access to pools, pickleball, tennis, and more. Explore over 130 miles of golf cart paths in this vibrant 55+ community featuring 700+ golf holes, 100+ pools, and endless clubs and activities. Just an hour from Orlando’s theme parks and near cruise ports, it’s the perfect mix of fun, comfort, and Florida sunshine!

Newer Villa in The Villages near Brownwood
Kick back and relax in this calm, stylish new villa in the Villages. It is within walking or a 3 minute golf cart ride to Brownwood Town Center where there are dining, shopping and nightly music. It is also near Lake Okahumpka Recreation Center where you can fish or kayak. This area has beautiful nature trails for walking or biking with separate golf cart paths. There is a neighborhood pool and other amenities nearby. It also comes with a complementary golf cart for your convenience.

Safari themed private addition with pool/hot tub.
This special Guest house addition is close to everything in The Villages! Making it easy to plan your visit.! We are in The Village of Osceola Hills at Soaring Eagle Preserve. A short golf cart or car ride to Brownwood Square and Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Access to play over 50 golf courses at a minimal fee. Ask us about our easy 4 seater Golf-cart rental and upon request free Guest passes!

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.

New home in the new part of the villages.
Beautiful new home in the villages. All new appliances with all brand new furniture, beds and decor. You have quick access to Sawgrass grove Entertainment facility, Ezell recreation center and McGradys pub. This open floor plan with the kitchen opening to living room keeps everyone together. The huge island is a great hanging out spot. You will have access to many close by, pools, shuffle board, parks and golf courses during your stay.

Lake Sumter 2/2 Villa FREE gas cart/Pet friendly
Super clean 2-bed/2-bath property in Buttonwood with free use of gas cart. Nicely furnished, with washer/dryer, smart tv and vaulted ceilings. This patio villa is in a highly desirable area within walking distance to the Fishhawk pool, rec center and many golf courses. Equal distance between Lake Sumter Landing & Brownwood squares. $89 pet fee. 4 person cart available at $50/day. 2 person cart is free. Return cart full please.
Popular amenities for The Villages rentals with a pool
House rentals with a pool

Pool Home Great Location 3/2 & 2 Golf Carts

PATIO VILLA W/ GOLF CART CLOSE TO LAKE SUMTER LAND

KingBed w/Cart

Waterfront, Heated Pool, Golf Cart, & 2 King Beds

Heart of The Villages-guest pass for pool, golf

Patio Villa - Pet Friendly 2/2 Home (South of 44)

Sunset Oasis - 3/2 w/ Pool & Golf Cart

BrandX Premium - 1921 McMurtrie
Condo rentals with a pool

20 Mi to Disney: Condo w/ Pool Access in Clermont!

1 Bedroom 5-Star Standard Resort Villa Near Disney

Wafflemaker Waterfront condo 2BR full ensuite pool

Cypress Cove Waterfront Townhome

Beautifal 2 Bedroom 5-Star Grand Villa

1 Bedroom 5-star Grand Resort Villa Near Disney
Other vacation rentals with a pool

StJohns is a great area for golf, hiking, Kayaking

Spotless Villa Near Brownwood Sq- Lanai & King Ste

Villages - Priv. Htd. Pool 3BR/2BA, Conv. Location

Heated Pool Golf Cart Dog Friendly in The Villages

The Sunshine Retreat with Golf Car

Lazy Day Getaway*New Const*2bd/2ba*Pet Friendly

Pool & Bar Oasis: 3-BR House Near Horse Parks

The Caddy Shack, Heated Pool, 4 seater golf cart
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.ﺇ639 | ﺩ.ﺇ679 | ﺩ.ﺇ661 | ﺩ.ﺇ474 | ﺩ.ﺇ452 | ﺩ.ﺇ433 | ﺩ.ﺇ386 | ﺩ.ﺇ375 | ﺩ.ﺇ422 | ﺩ.ﺇ433 | ﺩ.ﺇ499 | ﺩ.ﺇ521 |
| 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 |
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.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 7,790 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 110 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!
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Weeki Wachee Springs
- Aquatica
- ICON Park
- Disney's Hollywood Studios
- Island H2O Live!
- Camping World Stadium
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- Shingle Creek Golf Club
- Universal's Islands of Adventure
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