Holiday rentals with a pool in Wildwood

4.96 out of 5 average rating, 326 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.

4.98 out of 5 average rating, 412 reviews

The inviting exterior features a two-story home framed by lush green grass and mature trees. Arched windows and a symmetrical design enhance the charm, while a driveway leads to the front entrance, providing easy access to the peaceful surroundings.

Guesthouse in Leesburg

Silver Lake Guest Pool House Very Private !

The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from grocery stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

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!

Superhost

A screened-in pool area is highlighted, featuring a sparkling blue pool surrounded by a stone patio. Greenery is visible beyond the enclosure, contributing to the serene environment. A single lounge chair is positioned beside the pool, evoking a relaxing atmosphere.

Home in Ocala

4.82 out of 5 average rating, 126 reviews

Spacious 3BR home with HEATED POOL in Ocala

Relax and hang out with the whole family in this beautiful Ocala house! Soak up some sun in the screened in pool and lounge chairs, or enjoy the mini basketball court and outdoor grill. Just 25 min to the World Equestrian Center, it’s the perfect oasis to stay in while you or your family compete. Enjoy some peace and quiet with a short 20 min drive to a vibrant downtown. Just 5 min to the Marion Oaks Community Center with tennis and other activities, there is something here for everyone!

4.95 out of 5 average rating, 105 reviews

A charming single-story home is set on a lush green lawn, surrounded by trees and landscaping. A welcoming front porch features a swing and a bright blue door, adding a touch of color to the natural surroundings.

Home in Ocala

Ocala Oasis-3 Bedrooms and Heated Pool!

Relax in a safe neighborhood with a pool home that boasts 3 bedrooms and a game room with air hockey/pool/Foosball table. There is a outdoor Basketball hoop, ample pool side seating, fire pit, and kayaks for exploring The Silver Springs, which are 6 miles away. This home is spacious, quiet, and clean. Just minutes from downtown and 12 miles from World Equestrian Center. Have fun grilling by the pool or venturing out on the town. This home is central to everything Ocala has to offer.

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, 64 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.

Superhost

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

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.

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, 37 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, 106 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 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, 80 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, 137 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

A wooden boardwalk winds gracefully along the edge of a tranquil waterway, surrounded by lush greenery and mature trees. Nearby, a pavilion stands, offering shaded views of the serene landscape, enhancing the outdoor experience.

4.94 out of 5 average rating, 17 reviews

StJohns is a great area for golf, hiking, Kayaking

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.

A heated pool is featured with a smooth, curvaceous shape and clear water reflecting surrounding shadows. Access is provided by steps leading into the water. The pool area is enclosed by a screen, allowing views of the lush green yard and nearby homes.

5 out of 5 average rating, 41 reviews

Pool Home Great Location 3/2 & 2 Golf Carts

A spacious screened lanai features comfortable seating arranged around a glass-top table. Outdoor dining spaces with a large umbrella and views of the fenced yard and greenery are visible in the background, providing a serene setting for relaxation.

5 out of 5 average rating, 5 reviews

Huge & luxurious home w/view of preserves & fenced

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, 56 reviews

Village of Deluna at Marsh Bend 3bd 2bth

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!

4.86 out of 5 average rating, 21 reviews

Dreaming of DeLuna

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, 97 reviews

Fabulous Courtyard Villa close to Sumter Landing

Condo rentals with a pool

Condo in Kissimmee

HICV @ Orange Lake Resort 2BR Suite Saturday Check

4.92 out of 5 average rating, 38 reviews

The exterior view showcases a well-maintained townhome with a warm orange facade, complemented by palm trees. The entrance is marked by a covered porch flanked by tall white columns. A neatly arranged parking area is visible in front, providing convenient access.

Condo in Clermont

TinkerBell’s Townhome 3BR & 3BA w/ a heated Pool

An open living and dining area features a modern glass dining table surrounded by four chairs. A comfortable seating arrangement is situated nearby, illuminated by natural light from sliding glass doors that lead to an outdoor space. Soft décor elements create a welcoming environment.

Condo in Hernando

Heated Pool: Citrus Hills Condo Near Golfing!

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!

Superhost

A vibrant view of the resort shows modern buildings lined along a sandy beach area. Bright yellow umbrellas provide shade over white lounge chairs, while palms add greenery to the beachside setting. The clear blue water enhances the tropical atmosphere.

Condo in Orange County

4.75 out of 5 average rating, 8 reviews

4 Bedroom Luxury Flat in Orlando, FL near Disney!

4.81 out of 5 average rating, 16 reviews

A serene swimming pool area is framed by lush greenery and overlooks a calm body of water. Comfortable blue lounge chairs are arranged around the pool, complemented by potted plants. The clear sky and surrounding nature create a peaceful outdoor setting.

Condo in Dunnellon

River Retreat

Condo in Lake Buena Vista

An aerial view of a resort complex is displayed, featuring multiple buildings arranged around a serene lake. The buildings showcase varied architectural styles and are surrounded by lush greenery. A fountain can be seen in the lake, contributing to the tranquil setting.

4.82 out of 5 average rating, 11 reviews

Family friendly 2BR resort near Disney!

4.87 out of 5 average rating, 68 reviews

The exterior of Wyndham Bonnet Creek Resort is showcased, featuring a multi-story building surrounded by lush palm trees and an inviting pool area. The image includes a vibrant presentation with a character from Disney, emphasizing the family-friendly atmosphere of the resort.

Condo in Orlando

Wyndham Bonnet Creek ツ 1 Bedroom Deluxe!

Home rentals with a private pool

A spacious living area features light-colored walls and plush carpeting. Two comfortable sofas with decorative pillows face a wooden coffee table. A large flat-screen TV is mounted on the wall, and natural light enters through sliding glass doors, which lead to an outdoor area.

Villa in Clermont

3 Bedroom Private Pool with Spa Near Disey

A large pool area is depicted, featuring a prominent metal heron sculpture beside the water. Solar panels are visible on the building in the background. The pool is surrounded by white fencing and offers multiple seating and lounging options.

3 Bed Town Home with Splash Pool!

A contemporary living area is shown with a sectional sofa featuring colorful cushions. A round glass coffee table rests on a circular area rug. A large abstract painting complements the neutral walls, and a wall clock adds a modern touch.

3bed Villa 10 Mins to Disney-17440 Serenity Resort

A private screened pool area features a clear blue pool complemented by a spa that is heated to match the pool temperature. Sun loungers are positioned along the edge, surrounded by lush greenery and a well-maintained landscape.

Villa in Clermont

Glenbrook Lovely 4 Bed Pool/spa Home!

A two-story vacation home is shown, featuring a light-colored facade with palm trees and vibrant landscaping. The driveway presents designated parking areas, complemented by neatly trimmed grass and colorful shrubs, creating a welcoming entrance to the property.

Serenity 3 Bed Townhome

The two-story vacation home is shown with a charming orange façade. Lush palm trees provide shade in front of the well-maintained garden. A welcoming porch area includes two chairs, and the sidewalk leads to the entrance, enhancing the inviting appearance of the property.