Holiday rentals with a pool in Wildwood

4.96 out of 5 average rating, 331 reviews

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.

Home in Lady Lake

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.

A charming home exterior showcases a light blue facade and a white picket fence, surrounded by vibrant landscaping. A two-car garage is positioned prominently, with decorative plants adding interest. The clear blue sky provides a bright backdrop, accentuating the inviting appearance of the house.

4.97 out of 5 average rating, 31 reviews

Brownwood Square - Villages Home

Indulge in a stylish retreat at this centrally located home, just minutes from the vibrant Brownwood Square in the sought-after Village of DeLuna. Immerse yourself in the full Villages experience with a community pool, recreation center, and included golf cart—perfect for exploring. Enjoy nearby shopping, dining, live music, nightlife, sports, and more. Explore Central Florida or take a short drive to the Gulf Coast, Atlantic Ocean, Disney, or Orlando’s vibrant attractions—all within an hour!

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, 88 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.

The exterior of the home showcases a light gray façade with a welcoming front porch. Lush green grass is framed by neatly arranged flower beds, while a flagpole displays the American flag. A paved driveway leads to the entrance.

4.96 out of 5 average rating, 68 reviews

2/2 Villa in Citrus Grove - Rates Reduced!

*Redone in 2023* - 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!

The exterior of a modern single-story home is showcased at twilight, featuring a neatly landscaped front yard with tropical plants. A cozy seating area is visible by the entrance, and a two-car garage complements the home’s facade under a colorful sunset sky.

4.67 out of 5 average rating, 6 reviews

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!

A stylish villa exterior is presented with a gray facade and a welcoming porch area. A well-maintained lawn features a white picket fence and newly planted shrubs. A golf cart is parked on the driveway, ready for use, while the surroundings depict a tranquil neighborhood setting.

4.97 out of 5 average rating, 69 reviews

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.

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, 10 reviews

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

4-seat golf cart included. Well-located home in The Villages, 5 minute golf car ride to Eastport and Middleton. Literally a 2 minute walk to Shady Brook Adult Pool, 5 minute walk to Saluki Rec Center's Family Pool with pickleball courts, and indoor games like classic video games tables, billiards, pinball machine, darts, table tennis, etc. Multiple golf courses, easy access to Sawgrass Grove or Brownwood town squares' nightly music, dancing, dining choices at many great restaurants.

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, 105 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!

4.85 out of 5 average rating, 114 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 the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.

4.97 out of 5 average rating, 102 reviews

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.

A single-story house features a white exterior with a gabled roof and a two-car garage. A white picket fence and manicured shrubs border the front yard, while a concrete driveway provides ample parking space. Clear blue skies are visible in the background.

4.96 out of 5 average rating, 82 reviews

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.

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, 139 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 Wildwood rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 3 reviews

5-Star Luxury | Prime Location & Top Amenities

A single-family home is depicted with a large driveway leading to a two-car garage. A covered front porch with white railings is visible, framed by neatly trimmed shrubs. The exterior features light-colored siding and blue window shutters, set against a backdrop of a well-maintained lawn.

4.95 out of 5 average rating, 19 reviews

Welcome to the Villages

A single-story home is depicted in a well-kept neighborhood, featuring a manicured lawn with palm trees and shrubs. Two vehicles, including a golf cart, are parked in the driveway, while a cloudy blue sky provides a serene backdrop.

4.95 out of 5 average rating, 103 reviews

FREE Golf Cart + Fabulous Location + Classy Decor!

An aerial view of the villa showcases its well-maintained exterior with a pitched roof and a combination of light yellow and gray hues. A screened lanai can be seen, along with a spacious outdoor patio area. Lush greenery and colorful flower beds enhance the welcoming curb appeal.

5 out of 5 average rating, 11 reviews

Slice of Paradise! Great location in The Villages!

A single-story home features a simple façade with a covered entryway and a spacious driveway. Lush green grass borders the driveway, complemented by small landscaping elements. The neighborhood displays well-maintained properties on either side, under a clear blue sky.

4.97 out of 5 average rating, 63 reviews

The Sunshine Retreat with Golf Car

A single-story home is showcased with a well-maintained front yard, featuring manicured grass and small landscaping elements. The exterior is designed with a light-colored facade, and large windows reflect the evening sky's hues. A two-car garage is included, along with a spacious driveway.

5 out of 5 average rating, 30 reviews

BrandX Premium - 1921 McMurtrie

5 out of 5 average rating, 15 reviews

Newest Hotspot in The Villages Eastport/Middleton”

4.95 out of 5 average rating, 21 reviews

Outdoor Fun at the Pool + 2 Golf Carts!

Condo rentals with a pool

A spacious outdoor area features several palm trees and seating arrangements with turquoise cushions. The backdrop includes a modern multi-story building. A barbecue area is visible, and lounge chairs are positioned around a sparkling pool, creating an inviting environment for relaxation.

4.89 out of 5 average rating, 124 reviews

Luxury Condo On I-Drive & One Mile from Universal

A cozy living area features a spacious gray sofa positioned in front of a large window, allowing natural light to fill the room. A decorative vase of vibrant flowers is placed on a dark dining table. A wall adorned with imagery adds character to the space.

4.82 out of 5 average rating, 466 reviews

Amaranta/Studio beautiful balcony LAKE VIEW 🫶❤️

An aerial view of the clubhouse area is displayed, featuring a large pool surrounded by lounge chairs. Palm trees provide greenery around the poolside, while guests can be seen enjoying the water. The architecture of the clubhouse complements the inviting outdoor space.

4.92 out of 5 average rating, 131 reviews

Location,Location 3bd 2bth near parks conv.ct/Int.

A warm living space features a dark wooden ceiling and an accent wall with textured concrete. Comfortable seating faces a mounted television, while wooden shelves are adorned with books and decorative plants. Natural light enters through large windows, enhancing the inviting atmosphere.

4.87 out of 5 average rating, 112 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

A dining area features a wooden table set with plates and glassware, complemented by blue and white patterned napkins. A modern pendant light illuminates the space, while decorative plants and artwork add a touch of style to the inviting atmosphere.

4.95 out of 5 average rating, 172 reviews

VCR1-204 Deluxe Condo - Convention Center

A spacious bedroom features a queen bed with a light gray throw blanket and decorative pillows. Twin beds are visible in the background, while artwork adorns the wall. Two bedside lamps and wooden nightstands flank the bed, complementing the warm wooden flooring.

4.9 out of 5 average rating, 135 reviews

The Point Hotel & Suites - 705H Luxury - Pool View

A spacious terrace features comfortable lounge chairs with blue cushions and a stylish hanging chair. A small table accompanies two chairs, providing a perfect spot for relaxation. An umbrella offers shade, while the expansive view overlooks the surrounding area, enhancing the outdoor experience.

4.86 out of 5 average rating, 523 reviews

Lakefront Studio •Private Terrace• near Universal

A cozy studio space is highlighted by a spacious bed adorned with a decorative blanket. A comfortable sofa and tufted stool provide additional seating. Light floods in through large windows, illuminating the soft tones of the wallpaper and area rug.

4.88 out of 5 average rating, 180 reviews

Luxury Studio, Near to Universal-Epic ,And Disney!

Other holiday rentals with a pool

5 out of 5 average rating, 3 reviews

Home in Ocala

Beautiful 3BR Ocala Home | Perfect for Families

4.95 out of 5 average rating, 93 reviews

A bright yellow door features a decorative wreath made of colorful flip-flops and a large floral element. The door is framed by clear glass panels, with the words 'home sweet home' artfully displayed near the doorknob.

Home in Lady Lake

Magnolia Cottage under the Paradise sun.

4.95 out of 5 average rating, 38 reviews

A charming exterior of a single-story villa is depicted, featuring a well-manicured lawn with vibrant green grass and mulched beds. A neatly trimmed tree stands in front, alongside a colorful plant. A white picket fence encloses the yard, and a driveway leads to a single-car garage.

Villa in The Villages

PATIO VILLA W/GOLF CART 1M TO SQ-NO XTRA GUEST FEE

An open-concept living area showcases a cozy seating arrangement with a leather sofa, complemented by a large dining table. The well-equipped kitchen features modern cabinetry and appliances. Sunlight filters through the windows, illuminating the space and creating a welcoming environment.

4.93 out of 5 average rating, 57 reviews

Village of Deluna at Marsh Bend 3bd 2bth

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.

4.63 out of 5 average rating, 8 reviews

Beautiful home on golf course w/ unheated lap pool

4.98 out of 5 average rating, 50 reviews

The home's exterior features a vibrant orange facade with a neatly manicured yard and landscaping of tropical plants and colorful stones. A golf cart is parked in the driveway, providing convenient access to nearby amenities.

Villa in The Villages

Courtyard Villa On Golf Course w/Cart & Hot Tub

4.94 out of 5 average rating, 32 reviews

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

The exterior of a single-story home is shown, featuring a contemporary design with a two-car garage and a well-maintained lawn. The driveway is clear, and landscaping includes small shrubs and green grass leading to the front entrance under a covered porch.