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.

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Guest favourite

Villa in The Villages

4.98 out of 5 average rating, 54 reviews

Perfect location Lake Sumpter Villa w/ Golf Cart

Location, Location, beautiful 2 bedroom villa with 2-seater golf cart, is located in the desirable neighborhood of Creekside Landing. This villa is within walking distance of Lake Sumter Landing town square where you will find shopping, restaurants, a movie theater and FREE nightly live entertainment. Edgewater neighborhood Recreation Center with a pool, as well as Canal Street Recreation Center with activities such as shuffleboard courts, bocce courts, card rooms and so much more. This villa is beautifully decorated in a warm and inviting style. The kitchen is fully equipped with everything you’ll need to prepare meals and entertain friends. The living room offers plenty of comfortable seating with a flat screen TV. The master bedroom has a king size bed, flat screen TV, large walk-in closet and a private master bath with a walk-in shower, complete with towels and linens. The guest bedroom and guest bath comes completed with lines and towels for your guest’s comfort. There is a screened lanai with comfortable seating and a privacy wall . This villa comes complete with WiFi. With the purchase of resident ID cards you can use any of the 29 executive golf courses with no greens fees. You pay resident rates in greens fees at the 11 championship courses. You are also entitled to use any of the family- friendly and adult (30 and older) swimming pools, and organized activity swimming pools, There are over 1,000 organized activities each week through the recreation centers. Rates are based on double occupancy. Rates shown do not include taxes and additional fees

Nov. 8 – 15

$213 CAD per night

Guest favourite

Home in The villages Florida

4.97 out of 5 average rating, 207 reviews

The Village’s Coffee or cocktails on the course !

EXCELLENT ROBUST WI FI FOR THE ENTIRE PROPERTY . CHECK OUT TIME IS 10AM Wake up with Coffee or afternoon cocktails on the fifth hole of the Tierra Del Sol Country Club close to Spanish Springs and Lake Sumter Landing town squares. In the Village of Santiago. Free live music 365 days at each of three town squares. CLose to shopping, golf and pools. Enjoy day of golf, swimming, a country club dinner and dancing on the square NO smoking environment. NO children Also, no pets allowed.

Dec. 9 – 16

$230 CAD per night

Guest favourite

Villa in The Villages

4.87 out of 5 average rating, 71 reviews

Patio Villa Near BrownWood

Enjoy your beautiful Colony Patio Villa in PINELLAS. Near Brownwood Town Square, Eisenhower regional rec center, & Bonifay and Evan’s Prairie CCs. WALKING DISTANCE to Big Cypress, 3 executive courses, and PINELLAS PLAZA (with Winn Dixie, restaurants & more) January to March bookings must be for a full calendar month (beginning and ending on the 1st and last, respectively) The Villages is an Active 55+ Community. Young visitors are allowed for limited periods with plenty of family activities.

Aug. 31 – Sep. 7

$203 CAD per night

Guest favourite

Home in Lady Lake

4.97 out of 5 average rating, 270 reviews

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.

May 20 – 27

$162 CAD per night

Guest favourite

Home in The Villages

4.91 out of 5 average rating, 23 reviews

Beautiful Designer Home in The Villages Fl

The Home is in the Villages a gated golf cart retirement community. Golf, Music, Entertainment, Activities, Pools , its the Villages!! the home is a 2280 Sq ft living space 3 bdr each with a king size bed and Tv. 2 bath large lanai on the 2nd hole of the Tierra Del Sol golf course. A golf cart is available for a small extra fee. Washer and Dryer , Kitchen is stocked for all your cooking needs. Visit the Villages your Happy Place. I will send special offers for longer stays 2 weeks or longer!

Jul. 31 – Aug. 7

$192 CAD per night

Guest favourite

Home in The Villages

4.94 out of 5 average rating, 106 reviews

2/2 custom pool home with 4 person gas golf cart

Beautiful Monterey style home, 2/2, 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 for extra folks. 4 person gas golf cart. 2 bikes available but not maintained by owner. Sorry, hot tub not included. Pet friendly!

Aug. 11 – 18

$312 CAD per night

Guest favourite

Home in The Villages

4.94 out of 5 average rating, 108 reviews

Pool, golf cart, private backyard. Paradise!

Come and enjoy this relaxing piece of paradise surrounded by lush greenery with your own, small, private pool (not heated). "Serene on the Green" is a beautifully remodeled 3 bedroom, 2 bathroom designer home (1,536 sqft) with a large screened outdoor pool area with lots of privacy. Our location 320 steps from the Santiago Recreation Complex with two golf courses and a short ride to Lake Sumter Landing and Spanish Springs is perfect. A new custom 2021 Yamaha QuieTech golf cart is included!

Dec. 9 – 16

$389 CAD per night

Guest favourite

Home in The Villages

5.0 out of 5 average rating, 7 reviews

Central Villages w/ Golf Cart

Centrally located in The Villages. Use the included golf cart for a short golf cart ride away from 2 Town Squares (Brownwood and Lake Sumter Landing), where there is free nightly entertainment 365 nights/ year. The patio villa is well appointed, including a split-king adjustable bed in the main bedroom, queen bed in the guest bedroom. Tucked away at the end of the street, with a side patio w/ retractable awning and grill. Also screened in lanai w/ blinds. LVP throughout-no carpet.

Nov. 29 – Dec. 6

$232 CAD per night

Guest favourite

Home in Wildwood

4.93 out of 5 average rating, 28 reviews

*May Rates Reduced 2/2 in Village of Citrus Grove

*Newly Redone* - Brand new furniture throughout - Freshly painted - Screened in Lanai 2 Bedroom, 2 Bath located in Citrus Grove in The Villages, FL Great Location! - Very close to Citrus Grove adult pool - Homestead recreation center with family pool 0.7mi - Ezell Recreation Center 1.1mi - Sawgrass Complex 1.3mi There are several amenities for you to enjoy in The Villages - restaurants, bars, nightly live entertainment, shopping, golf, pickleball, shuffleboard, and so much more!

Jun. 16 – 23

$169 CAD per night

Guest favourite

Home in The Villages

4.92 out of 5 average rating, 130 reviews

Briar Meadow Villa

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. Access to The Villages amenities available for a $50 fee payable to The Villages. Golf Cart, Comcast cable TV, high speed WIFI, & Villages Daily Sun included.

Sep. 21 – 28

$206 CAD per night

Guest favourite

Home in The Villages

4.84 out of 5 average rating, 37 reviews

Villa la Bella

Stay in one of the most desirable locations in The Villages in the village of Sable Chase. Our beautifully remodeled and newly updated villa is just minutes from Sumter Landing in the heart of The Villages. Bright and airy feeling, tastefully designed and decorated, it features hardwood floors throughout. The 2BD, 2BA house with cozy lanai and new stainless gas grill also includes a Yamaha gas golf cart for your use. Your Villages vacation is ready for you at Villa la Bella!

Aug. 16 – 23

$136 CAD per night

Guest favourite

Home in The Villages

4.94 out of 5 average rating, 35 reviews

Beautiful Villages 2/2 Home. Perfect Location

Cozy 1,121 Square Feet single family home with everything you will need for a great stay at The Villages. Incredible location, only a 6 minute golf cart ride to Lake Sumter Landing and a 8 minute golf cart ride to Spanish Springs. All Villages amenities and 2 person gas golf cart included. Golfers Dream. Recreation centers, entertainment, pools and tons of activities all minutes away by drive or golf cart. One small dog under 20 pounds allowed, no cats.

Aug. 26 – Sep. 2

$163 CAD per night