Holiday rentals with a pool in The Villages

A well-maintained exterior of a single-story home is presented, featuring a light yellow facade and a welcoming front porch. Lush greenery and palm trees are positioned along the pathway, with a manicured lawn and trimmed shrubbery enhancing the curb appeal.

4.96 out of 5 average rating, 134 reviews

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

5 out of 5 average rating, 22 reviews

The private pool area is enclosed by a screened lanai, illuminated by string lights. A relaxing area features loungers beside the pool, with a raised spa and gentle water feature. Lush greenery surrounds the space, creating a serene atmosphere.

Villa in Lady Lake

Heated Pool Golf Cart Dog Friendly in The Villages

Nestled amidst lush greenery and shrubs ,Vida Rosa’s private pool provides a serene outdoor oasis, complete with a dining area, loungers, and a gas BBQ. The luxurious accommodations are thoughtfully designed to evoke a sense of calm and elegance. The flow between indoor and outdoor spaces offers an ideal retreat. Conveniently located, Vida Rosa is just a short golf cart ride away from the squares of Spanish Springs and Lake Sumter offering a variety of restaurants, shopping, and entertainment.

A decorative entrance sign for Villa De La Vista South is set against lush greenery and vibrant flowering plants. The sign stands prominently atop a circular flower bed, with a clear blue sky and soft clouds in the background.

4.92 out of 5 average rating, 13 reviews

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.

A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.

4.96 out of 5 average rating, 324 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.

5 out of 5 average rating, 5 reviews

Palm Tree Pad 3BR The Villages| Golfcart| Kingbed

We assure you of a relaxing stay in our BRAND-NEW home, situated just minutes from the best town squares in The Villages! With a four-seater electric GOLFCART and NEW AMENITIES, you will be minutes from Eastport Town Square, Saluki Recreational Center, Brownwood Paddock and top courses like Southern Oaks, Jubilee, Mickylee, Belle Glade, Red Fox & Grey Fox,etc. You'll also be minutes away from Alden Bungalows pool. Please be advised that a $50 charge is applicable to get the lifestyle IDs.

4.93 out of 5 average rating, 137 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!

An extended lanai features a dining table surrounded by cushioned chairs, with views of a heated saltwater pool and lush greenery beyond. Comfortable seating arrangements are designed for relaxation, while ceiling fans provide a gentle breeze throughout the open space.

4.99 out of 5 average rating, 82 reviews

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.

Place to stay in The Villages

An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.

5 out of 5 average rating, 97 reviews

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!

A heated saltwater pool is highlighted under a screened enclosure, with ambient lighting creating a calming atmosphere. Patio seating is arranged around the pool, and views of the adjacent living area are visible through expansive windows, enhancing the inviting indoor-outdoor connection.

5 out of 5 average rating, 34 reviews

Pirates & Parrots - The Villages - w/Golf Car !

GREAT LOCATION!! A beautiful 2 bedroom 2 bath home with a saltwater pool and a hot tub. 77 inch TV with sound system, and 2 car garage/golf cart . Outdoor bar with big screen TV with seating area and a second seating area outside the bird cage. TV’s in both bedrooms. Great out door living! Minutes to everything via golf car: Brownwood 12 Sumter 16 Sawgrass 19. 4 champ golf and 7 exec golf courses 5-10. Publix, Walmart 5 minutes Golf Car 2022 Yamaha included! No smoking!!

4.84 out of 5 average rating, 103 reviews

An exterior view of the patio villa showcasing a well-maintained façade. A garage door is located to the left, with a Yamaha gas golf cart parked on the driveway. A white picket fence and colorful flowers enhance the entrance.

Villa in The Villages

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.

The exterior of a single-story home is showcased, featuring a well-maintained lawn and a gravel pathway. A seating area with chairs is positioned on the front porch. The garage is visible on the right, and colorful clouds are present in the evening sky.

5 out of 5 average rating, 12 reviews

Incredi-Bill Jo's

Get ready for an incredible stay at our Incredi-Bill Jo's stylish and cozy pool home. You'll be steps away from world class shopping, dining, entertainment, sports, recreation and GOLF. This three bedroom home is close to all of the amenities that make The Villages the number one destination for active adults year after year. And to make your stay even more incredible, you'll have the convenience and use of a beautiful golf cart! Come and see what all the fuss is about!

A well-maintained exterior features a single-story villa with light grey siding and a simple gable roof. A gas cart is parked on the driveway, surrounded by neatly trimmed shrubs and gravel landscaping, adding to the property’s welcoming ambiance.

4.96 out of 5 average rating, 135 reviews

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

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The exterior of a single-story home is framed by three tall palm trees, set against a clear blue sky. A well-maintained lawn surrounds the entrance, which is highlighted by a neatly paved driveway and a two-car garage. The inviting front door features a large window.

5 out of 5 average rating, 23 reviews

The Mulligan House-The Villages

A large, heated pool is visible, featuring a shallow lounging area and surrounded by a spacious patio. Several lounge chairs sit nearby, with a dining table and chairs positioned for outdoor meals. Lush greenery and trees frame the area, enhancing the serene atmosphere.

5 out of 5 average rating, 27 reviews

The Palms. Luxurious, pool, golf/bird pond view

A spacious swimming pool is enclosed by a screen, featuring a stone wall with decorative water fountains. Lush palm trees surround the area, and the clear blue water reflects the sky and greenery, creating an inviting outdoor space.

5 out of 5 average rating, 20 reviews

Perfect home-families/friends in The Villages, FL!

5 out of 5 average rating, 10 reviews

Heart of The Villages-guest pass for pool, golf

A welcoming exterior view of a single-story home is presented, featuring a spacious driveway and a well-maintained landscape. Decorative elements, such as palm trees and shrubbery, surround the entrance. The sky showcases soft hues of pink and blue during twilight, adding a peaceful ambiance.

4.89 out of 5 average rating, 9 reviews

Home with private pool, Tierra grande villas

An unheated lap pool is enclosed within a screen, featuring clear blue water. The deck is lined with turquoise patio chairs, inviting relaxation. Lush green trees and a golf course are visible through the screen, creating a serene outdoor view.

4.86 out of 5 average rating, 7 reviews

Beautiful home on golf course w/ unheated lap pool

5 out of 5 average rating, 24 reviews

A patio villa in Deluna, The Villages w/ Golf Cart

A private screened patio features two reclining lounge chairs positioned beside a small table. The pool is visible nearby, while a lush green landscape with palm trees is observable through the screen, offering a serene outdoor space.

4.97 out of 5 average rating, 88 reviews

Private Pool with Sunset View in Monarch Grove

Condo rentals with a pool

A comfortable living area features a spacious sofa adorned with colorful cushions and a glass coffee table. Natural light enters through large windows, illuminating the light wood floors. A ceiling fan and soft lighting create a relaxing ambiance, complemented by a nearby seating area.

Condo in Clermont

4.67 out of 5 average rating, 24 reviews

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

A large sign is displayed prominently, reading 'I Love Westgate' in bold letters. The sign is framed by lush palm trees and colorful landscaping, with a warm, inviting building visible in the background under a partly cloudy sky.

Condo in Kissimmee

1 Bedroom 5-Star Standard Resort Villa Near Disney

4.82 out of 5 average rating, 11 reviews

Condo in Inverness

Sparkeling Waterfront condo 2BR w full ensuites

4.87 out of 5 average rating, 62 reviews

The living area features two comfortable sofas adorned with decorative pillows, arranged around a patterned area rug. A dining set with wooden chairs is visible nearby, while a spiral staircase leads to the upper level. Ample natural light enters through multiple windows.

Condo in Inverness

Cypress Cove Waterfront Townhome

A large, colorful sign displaying 'I ♥ WESTGATE' is prominently placed in front of a multi-story building. Surrounding palm trees and landscaped greenery enhance the welcoming exterior of the Westgate Town Center. The backdrop features a clear blue sky with fluffy white clouds.

Condo in Kissimmee

50% Off Sale 2 Bedroom 5-Star Grand Villa

A large, colorful sign reading 'I Love Westgate' is prominently displayed in front of a multi-story building. The sign features a bold red heart, surrounded by lush palm trees and decorative landscaping that adds a tropical feel to the setting.

Condo in Kissimmee

1 Bedroom 5-star Grand Resort Villa Near Disney

Other holiday rentals with a pool

A private in-ground pool is enclosed by a screen patio, featuring a textured stone deck. Comfortable lounge chairs line the poolside, with a railing leading into the water. Lush greenery surrounds the area, offering a sense of tranquility and seclusion.

4.96 out of 5 average rating, 46 reviews

Beautifully Furnished 3/2 with In-ground Pool

The kitchen features modern stainless steel appliances and a large island with seating for four. The quartz countertops complement the rich cabinetry and vibrant blue wall. Pendant lights provide illumination, enhancing the sleek design of the space.

5 out of 5 average rating, 13 reviews

Designer Home in The Villages, FL.

The modern home features a spacious driveway leading to a large carport and a two-car garage. A covered porch with steps provides access to the front entrance, surrounded by greenery and trees.

5 out of 5 average rating, 49 reviews

Villages home with unique elevated front porch

The exterior of a contemporary home is illuminated at night, showcasing a well-maintained lawn and landscaping. Details include a spacious driveway leading to a two-car garage and a warm light fixture by the entrance, highlighting the inviting path to the front door.

5 out of 5 average rating, 13 reviews

Begonia on the Bend – Stylish Home Near Sawgrass

A large outdoor pool is surrounded by a spacious deck, featuring neatly arranged lounge chairs. Palm trees are visible in the background, and a covered area with seating can be seen to the left. The sky features a mix of soft blue and wispy clouds.

5 out of 5 average rating, 7 reviews

2 min walk to pool, 4 seat cart, 5 min to Eastport

The front of a single-story home is presented, featuring a covered porch with two colorful chairs. A decorative mailbox is visible, and a blue truck is parked in the driveway. The lawn is neatly maintained, with shrubs lining the walkway.

4.98 out of 5 average rating, 46 reviews

Relaxing House in The Villages

The front view of the home shows a well-maintained exterior with a driveway accommodating two vehicles and a parked golf cart. Lush green landscaping enhances the welcoming appearance.

4.95 out of 5 average rating, 98 reviews

FREE Golf Cart + Fabulous Location + Classy Decor!

The image displays a bright, welcoming ambiance created by soft natural light filtering through sheer curtains. Beautiful yellow flowers in the foreground draw attention, emphasizing the inviting aesthetic. Decorative text presents key features of the Margarita House, including spaciousness and views of the backyard.