Holiday rentals with a pool in Haines City

A private pool area is enclosed by a screened lanai, featuring lounge chairs and a dining table under a shaded overhang. Colorful pool floats rest on the water's surface, while greenery surrounds the space, enhancing a relaxed outdoor atmosphere.

4.79 out of 5 average rating, 68 reviews

Pool Home Near Disney in Premier Golf Community!

Welcome to your dream retreat! This 3BR/2Bath home, nestled in a gated golf and country club community, offers the perfect getaway. Accommodating up to 8 guests, it features a private pool for endless relaxation and fun! Experience luxurious living, all in close proximity to Disney World and the best that Central Florida has to offer. Whether you're lounging by the pool or enjoying Southern Dunes' renowned golf course, this home provides the ultimate in comfort and leisure. Book your stay today!

A single-story home features a light blue exterior with neatly trimmed hedges and palm trees in the front yard. The driveway leads to a two-car garage, and large windows reflect natural light, enhancing the welcoming ambiance of the property.

4.95 out of 5 average rating, 177 reviews

Luxury Home 4/3 near Disney, 2 Masters

Luxury 4 bedroom home located in a quiet, gated community about 15 miles from Disney World. The travel time to Disney will depend on the traffic but is usually between 30 and 40 minutes. Fully furnished with 2 master King bed suites, one queen bedroom and one bedroom with 2 twin beds. 3 full baths. 5 high definition televisions, high speed Wifi, free long distance phone calls to US, Canada and UK. Large pool and spa. Large game room with many games and activities for children of all ages.

The exterior of the home features a light-colored facade with a welcoming entrance. A neatly landscaped yard includes vibrant green shrubs and a palm tree. The driveway leads to a single-car garage with a white door, set against a backdrop of clear blue skies.

4.91 out of 5 average rating, 201 reviews

Southern Dunes Villa - Pool - Golf - near Disney

Stunning executive home with a south facing screened in-ground pool overlooking the 2nd hole of the Southern Dunes Golf Course. 13 miles from LEGOLAND, 22 miles from DISNEY, 29 miles from UNIVERSAL, this is the perfect place to relax after a busy day at the parks. Impeccably maintained, our villa features upgraded furniture, electronics, mattresses and flooring. Southern Dunes is a gated golf community that prides itself on the quality of its golf course & the security & beauty of its homes.

A screened-in pool area features a clear, inviting swimming pool surrounded by comfortable lounge chairs. A basketball hoop is positioned at one end of the pool, with a scenic view of the lake and trees visible through the enclosure.

4.96 out of 5 average rating, 101 reviews

Southern Dunes Lakeview Poolhome

Highlights… Lake view, extra comfortable mattresses, purified drinking water, loads of toys, lego tables, train table, children’s books, sports equipment, pack n play, baby stuff & game room! Retreat to the pool area of this beautiful, 4-bedroom home conveniently located between Legoland and Disney World in the sought-after Southern Dunes golf course! This gorgeous gated community with 24h security is the perfect place to unwind and take early morning strolls through the neighborhood.

A two-story, tropical style home is showcased, featuring a vibrant exterior in warm shades. A Tesla is parked prominently in the driveway, with lush palm trees and greenery flanking the entrance. The garage is accessible, contributing to the property's inviting curb appeal.

4.92 out of 5 average rating, 111 reviews

Luxury Tropical Themed Villa With Lake View!

Just a half-hour from Disney and other major theme parks, this beautiful Tropical style home has a sunset lake view and was recently renovated with brand new furniture! The house resides comfortably in a gated community with 4 bedrooms and 3 bathrooms in a 2-story, 1700 square foot tropical setting! A private heated pool and Tesla charging is also accessible at the home. The Southern Dunes community boasts a large public golf course within a few minutes walk through the neighborhood!

4.89 out of 5 average rating, 133 reviews

Breathtaking Home

New two story home with private pool, patio, barbecue area & game room. Surrounded by parks, gardens, tranquil lakes & walkways with breathtaking views. Resort amenities located right across the street with an amazing clubhouse (private owned), Bar & Grill restaurant, water park, arcade and gym (extra fee), soccer & football field, & event center for parties & weddings. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

4.82 out of 5 average rating, 157 reviews

KokomoVilla: 4BR Southern Dunes Pool Home

Southern Dunes vacation rental in Haines City, Florida, KokomoVilla is a spacious 4-bedroom, 3-bath pool home overlooking Southern Dunes Golf & Country Club. This family-friendly vacation rental sleeps up to 10 guests and features a private screened pool, golf course views, and a prime location between Disney and Legoland. Ideal for golf trips, family vacations, and extended Central Florida stays, KokomoVilla offers comfort, convenience, and resort-style relaxation.

4.95 out of 5 average rating, 21 reviews

Themed Pool Home b/w Disney- Legoland | Golf Resor

Modern 4BR/3BA pool home in a secure, award-winning golf resort between Disney & Legoland. Sleeps 10 across 6 beds — 1 king master suite, Star Wars & Encanto themed kids’ rooms, plus a flex room for movies/play. Private screened pool (heat +$25/night), fully equipped kitchen, dining for 10, 65” living room TV. 17mi to Disney, 15mi to Legoland. 24/7 gated security, contactless self check-in. Onsite golf, restaurant & mini top-golf. Your own resort within the resort!

A well-maintained villa is showcased, featuring a welcoming entrance with a single-car garage. Lush greenery and colorful shrubs line the brick pathway, while tall palm trees and vibrant landscaping enhance the cheerful exterior. Bright clouds are visible in a clear blue sky.

4.86 out of 5 average rating, 181 reviews

Sandy's Southern Dunes Villa

This villa is in the Southern Dunes Golf & Country Club, which is an immaculately kept, secure complex, which maintains a 24-hour manned gate, making this a safe place to stay. There are community swimming pools, tennis courts, a gym, library and children's playground for those days when meeting Mickey Mouse is just too much trouble. With a Super-Walmart a minute away plus Dicks and several well-known restaurants just further away, virtually everything is on hand.

A spacious screened-in patio features a refreshing pool surrounded by a deck. Sun loungers are positioned nearby for relaxation, while lush greenery is visible through the transparent enclosure. The sky above shows a mix of clouds and sunlight.

4.86 out of 5 average rating, 83 reviews

Villa Bermuda, Orlando

During your stay in Orlando Florida, why spend your holidays in a small cramped hotel room when you can stay in a house? Located from 15 minutes from several parks in the area such as Disney, Universal Studios, legoland, sea world. This house is located on one of the most beautiful golf in Florida (Top 5) in the amazing community of Southern Dunes, with a 24 hour gated community and guardian . This luxury spacious house for rent is fully equipped!

5.0 out of 5 average rating, 10 reviews

4BR Near Disney & Legoland & Epic | Pool Table

Cozy tropical 4BR home sleeps 8 - perfect for Disney getaways, golf trips & family vacations! Just 30 min to Walt Disney World & LEGOLAND, 45 min to Universal and EPIC, 35 min to SeaWorld. Enjoy fast WiFi, free parking, Smart TVs, fully equipped kitchen, washer/dryer & pool table. Community pool access plus golf nearby at Southern Dunes Golf & Country Club and Providence Golf Club. Near Lake Eva Sports Complex, lakes, fishing & nature spots.

4.77 out of 5 average rating, 127 reviews

An inviting outdoor space features a gently curving pool with a built-in hot tub, surrounded by a screened enclosure. Comfortable lounge chairs are arranged nearby, with two patterned hammocks and a dining area visible in the background. Soft evening colors fill the sky above.

Home in Davenport

There is no other place you want to be than here.

✨ Experience Orlando in style! This 4BR, 3,100 sq. ft. retreat is just 10 min from Disney. Enjoy your own private pool, hot tub, and full sun all day in a quiet upscale community. Bright open living, chef’s kitchen, and spa-inspired relaxation make it the perfect escape after the parks. Pets welcome at no extra charge. Close to shops, dining, and attractions—book your luxury getaway today!

Popular amenities for Haines City rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.9 out of 5 average rating, 105 reviews

The image displays the exterior of a single-story home, featuring a combination of light and dark siding. A neatly paved driveway leads to a white garage door. Lush green landscaping, including ornamental plants and shrubs, borders the entrance, enhancing the home's inviting appearance.

Home in Davenport

Lovely Bridgeford Crossing

An inviting outdoor space features a private swimming pool surrounded by a sun deck with lounge chairs. A glass-top dining table is set for four beside a BBQ grill, with green views beyond the screened enclosure.

4.84 out of 5 average rating, 145 reviews

Southern Dunes Golf Vacation Villa

A private pool area features a screened enclosure, showcasing a clear blue pool surrounded by sunbeds. Lush greenery and tall trees are visible beyond the pool deck, creating a serene atmosphere. The space is designed for relaxation and overlooks the golf course.

4.75 out of 5 average rating, 52 reviews

Pool home located on Golf Course

The exterior of the villa showcases a two-story home with a light-toned facade. Lush greenery surrounds the entrance, featuring a palm tree and vibrant shrubs. A welcoming blue front door and decorative architectural details, including arched windows, enhance the home's curb appeal.

5.0 out of 5 average rating, 34 reviews

4bed pool /Hot tub,Game Room at Calabay Tower lake

The exterior of a single-story home features a manicured lawn with decorative flower beds. A spacious driveway leads to a two-car garage with an attractive door. The entrance showcases a covered porch, framed by decorative windows and a well-maintained landscape.

4.93 out of 5 average rating, 14 reviews

Posh and Peaceful Golf Resort Gate Home w Pool

An inviting outdoor space features a heated saltwater pool with a jetted spa. A spacious patio is surrounded by a screened enclosure, while comfortable seating and playful egg chairs provide relaxation options. Lush greenery and bright blue skies enhance the area's open feel.

4.92 out of 5 average rating, 52 reviews

Southern Dunes Home w/ Pool, Spa & Game Room

4.79 out of 5 average rating, 43 reviews

Lakefront HOME •POOL•Golf Course•Pets OK!

A private pool area is enclosed by a screened lanai, featuring a clear blue swimming pool. Lounge chairs are placed beside the pool, and a grassy area is visible beyond the enclosure, framed by tall trees under a partly cloudy sky.

4.84 out of 5 average rating, 51 reviews

Vacation Villa in Haines City

Condo rentals with a pool

A modern kitchen is featured with elegant cabinetry, stainless steel appliances, and granite countertops. A dining table is positioned to the left, surrounded by several chairs. Natural light enters through a nearby doorway, enhancing the sleek tile and hardwood flooring throughout the space.

4.92 out of 5 average rating, 101 reviews

Gated resort minutes from all major attractions

A living area features a gray sofa adorned with colorful pillows, a striped area rug, and two green armchairs. A wooden entertainment unit holds a large TV, while natural light filters through large windows dressed in sheer curtains, providing a connection to the outdoors.

4.89 out of 5 average rating, 175 reviews

ChampionsGate Tuscana Resort - Minutes to Disney!

4.88 out of 5 average rating, 115 reviews

Luxurious living just 15 min/Disney.

4.87 out of 5 average rating, 148 reviews

A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.

Condo in Kissimmee

Stylish Condo 20 mins to Disney/King Bed

A resort-style pool area is surrounded by palm trees and lush landscaping, with inviting lounge chairs arranged nearby. The clear water reflects a bright sky, and a separate lounge area with a decorative façade is partially visible in the background.

4.85 out of 5 average rating, 183 reviews

Orlando Spacious 2 Suites & Resort-Style Pool

The living room features a comfortable sofa and two accent chairs, complemented by a wooden coffee table. A flat-screen TV is mounted on the wall, and natural light fills the space from sliding glass doors that lead to a private outdoor area.

4.9 out of 5 average rating, 364 reviews

Amazing 2 Bed, 2 Bath condo only 10 min to Disney

A spacious bedroom features a plush, tufted headboard and a large window allowing natural light to fill the room. Two bedside lamps provide additional illumination, while modern furnishings add contemporary flair. A round mirror is mounted above the bed, reflecting the inviting ambiance.

4.79 out of 5 average rating, 274 reviews

Brand New AwardWinning Renovated Condo Near Disney

A welcoming living area is highlighted with a comfortable, light-toned sofa adorned with patterned cushions. An open layout leads to a modern kitchen, visible in the background, while ambient lighting creates a cozy atmosphere. Entertainment options are displayed, including Smart TV access to various streaming services.

4.83 out of 5 average rating, 355 reviews

3/2 Lake View King Bed Disney Family Condo Resort

Other holiday rentals with a pool

4.57 out of 5 average rating, 47 reviews

SD2133MC - Golf Course View Big Pool

4.88 out of 5 average rating, 40 reviews

Lakeview Villa • Private Pool • 4 En-Suites

4.83 out of 5 average rating, 24 reviews

Ideal location on a golf complex (343830)

A charming two-story home is displayed, featuring a light blue exterior and a welcoming entrance. Lush green landscaping surrounds the front, complemented by palm trees. A spacious driveway leads to the entrance, providing access to the property.

4.96 out of 5 average rating, 25 reviews

Skyblue Villas

An inviting outdoor space features a large private pool surrounded by a spacious patio. Comfortable seating options are provided, along with a shaded area for relaxation. String lights enhance the ambiance, and the pool is enclosed by a screened-in structure, offering a sense of privacy.

4.92 out of 5 average rating, 66 reviews

4BR Family Villa with Private Pool near Legoland

Bungalow in Southern Dunes Golf and Country Club

A single-story villa is presented with a pale yellow exterior, accented by white trim. A paved driveway accommodates a parked vehicle, while landscaped greenery enhances the front yard. Large windows create an inviting entrance, and a charming porch provides a welcoming touch.

4.89 out of 5 average rating, 73 reviews

TOP CLASS 4 bedroom villa near Disney area

A single-story home is showcased, featuring a light-colored exterior and a neatly landscaped front yard. Lush palm trees and shrubs enhance the lush green lawn. A driveway leads to a garage, while clouds drift in a clear blue sky overhead.

5.0 out of 5 average rating, 74 reviews

La Casita in Kokomo Bay