Holiday rentals with a pool in Haines City

5 out of 5 average rating, 21 reviews

Cozy 4BR Getaway Near Disney & Legoland

✨ Just about 30 mins from Disney, 20 mins from LEGOLAND®, and under 1 hour from Universal, Blue Paradise combines comfort, style, and an unbeatable location in the heart of Florida. Nestled inside the gated Southern Dunes Golf & Country Club, guests enjoy exclusive access to the golf course, fitness center, and children’s playground, plus convenient walking distance to Walmart, CVS, and local restaurants. A peaceful, family-friendly retreat perfectly situated close to all the magic of Orlando.

The exterior of the villa is showcased, featuring a two-story structure with a brown-tiled roof and large windows. A landscaped yard with greenery and flowers is visible, along with a cobblestone driveway leading to a dark garage door.

5 out of 5 average rating, 38 reviews

Florida Dream Home

🏡 Welcome to Florida Dream Home ✨ A stunning 4-bedroom villa with a private pool 🏊, located in a gated community just 15 minutes from LEGOLAND and 30 minutes from Disney🏰 Enjoy bright, spacious living areas, a fully equipped kitchen 🍽️ and cozy bedrooms 🛏️, each with an en-suite 🚿 Relax by the pool, dine on the deck, or explore nearby attractions 🎢 Perfect for families, groups and snowbirds, our home is designed for comfort, fun, and unforgettable memories. Your adventure starts here⭐️

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 out of 5 average rating, 65 reviews

La Casita in Kokomo Bay

Welcome to your dream vacation home! This stunning residence, nestled in a gated community, offers the perfect combination of comfort, style, and luxury living. With 3 bedrooms and 2 bathrooms, this home is designed to meet all your vacation needs.House features brand new kitchen and upgraded bathrooms Washer and dryer.Private sparkling swimming pool Enjoy the amenities and convenience of golf and just a short 25 minute drive to Disney World and many other attractions central Florida has . Hide

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, 169 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.

4.9 out of 5 average rating, 192 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.

5 out of 5 average rating, 12 reviews

Southern Dunes Family Retreat/Pool

Welcome to this modern 5-bedroom, 3-bath vacation home: • Located in a secure, award-winning golf community. Between Disney and Legoland. • Two master suites with private bathrooms • Modern renovated interiors • Themed kids’ rooms (Star Wars + Encanto) • Private heated pool, heat additional fee $25 • Sleeps 10 comfortably • Fully equipped kitchen & large dining area • 24-40 Minutes from Disney, Universal & Legoland • Contactless 24/7 self check-in This unique place has a style all its own.

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.

4.95 out of 5 average rating, 84 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, 95 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!

The two-story home is illuminated under a night sky, featuring clear glass windows that reflect soft light. Landscaped greenery surrounds the property, with a stone driveway leading to a garage. A large patio area is visible on the right side.

4.88 out of 5 average rating, 125 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.

A screened pool area features a private swimming pool, surrounded by modern lounge chairs. Tables and seating are available under a shaded area, providing a relaxing environment. The expansive view of the green golf course can be seen in the background.

4.93 out of 5 average rating, 14 reviews

House, backyard on the golf course Park Place

****RECENTLY RENOVETED IN 2023 March **** 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 with 3 bedrooms and 2 bathrooms with private pool , no rear neighbors, overlooking the golf course.

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, 170 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.

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.

4.83 out of 5 average rating, 138 reviews

Southern Dunes Golf Vacation Villa

This picture perfect executive villa is located within the Southern Dunes Golf and Country Club. This open concept villa includes 3 bedrooms that can comfortably accommodate up to 6 guests. This villa is located on the prestigious Southern Dunes Golf Course and offers guests a beautiful private swimming pool, outdoor dining area with a TV and BBQ within a fully gated community accompanied by 24 hr security at the front gate.

Popular amenities for Haines City rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An aerial view presents the stylish exterior of KokomoVilla, showcasing a well-maintained garden and driveway. The property is bordered by lush greenery and overlooks the golf course, with a sunset casting a warm glow across the sky, enhancing the serene atmosphere of the neighborhood.

4.81 out of 5 average rating, 151 reviews

KokomoVilla: 4BR Southern Dunes Pool Home

5 out of 5 average rating, 43 reviews

Home in Winter Haven

Luxury 3BR 2Bath•Pool• Game Room• Legoland 4 Min

5 out of 5 average rating, 9 reviews

Charming 3BR Home in Balmoral w/ Resort Perks

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, 49 reviews

Vacation Villa in Haines City

A single-story home is featured, showcasing a light-colored exterior with a well-maintained front yard. The driveway leads to a two-car garage, and a decorative mailbox stands at the curb. Lush greenery and shrubs frame the pathway to the entrance.

4.92 out of 5 average rating, 25 reviews

Golf Course Retreat

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 - free pool heat!

A vintage-style clock is mounted on the wall, featuring the iconic 'Platform 9¾' sign with a green light illuminating its face. The clock's circular frame is accented by a black metal bracket, adding a whimsical touch to the room's decor.

4.95 out of 5 average rating, 85 reviews

Harry Potter's 6bd 6.5ba Hogwarts Experience

5 out of 5 average rating, 17 reviews

Home in Davenport

Vacation Villa

Condo rentals with a pool

4.86 out of 5 average rating, 137 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 view of the pool area is visible from the second-floor balcony. The inviting pool features surrounding lounge chairs and well-maintained landscaping. The building's exterior is highlighted by stone accents, with a common area structure visible in the background, framed by greenery and pathways.

4.97 out of 5 average rating, 101 reviews

No Cleaning fee - 3 bed 3 full bath near Disney

4.87 out of 5 average rating, 102 reviews

The thrill of luxurious living just 15 min/Disney!

4.97 out of 5 average rating, 131 reviews

An open living space features large French doors leading to a balcony, allowing natural light to brighten the area. Stylish seating is arranged around a coffee table, while artwork resembling a Marvel theme decorates a wall in the adjacent bedroom. Views of palm trees and a nearby pool can also be seen.

Condo in Kissimmee

Golf Front Luxury Penthouse: Views, Marvel, 2Pools

A spacious dining area features a modern table set for six, complemented by a chandelier above. A living space is visible in the background, with a comfortable couch and large windows allowing natural light. Decorative elements include a floral arrangement on the table.

4.81 out of 5 average rating, 191 reviews

3BR/2BA Mediterranean Style Condo Near Disney

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.

4.84 out of 5 average rating, 164 reviews

Orlando Spacious 2 Suites & Resort-Style Pool

An aerial view showcases a large pool area surrounded by lush landscaping and palm trees. The complex features a main pool, children's pool, and several cabanas. The orange-roofed building provides a welcoming focal point, while the well-kept grounds invite relaxation and fun.

4.85 out of 5 average rating, 108 reviews

Spacious 2bd/2ba (No stairs) Disney/Championsgate

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, 168 reviews

ChampionsGate Tuscana Resort - Minutes to Disney!

Other holiday rentals with a pool

4.86 out of 5 average rating, 37 reviews

Private Pool Villa • Lake Views • Near Disney

The exterior of the spacious villa is presented, featuring a light-colored facade complemented by manicured landscaping. The corner plot is visible, with a driveway leading to a two-car garage. Lush greenery surrounds the home, contributing to the overall inviting appearance.

4.61 out of 5 average rating, 103 reviews

The Dunes at Southern Dunes Haines City

4.89 out of 5 average rating, 37 reviews

Cozy Calm Cottage

5 out of 5 average rating, 11 reviews

Family 3BR Pool Home Near Disney w/ Private Patio

5 out of 5 average rating, 52 reviews

5bd Villa Eman Private Pool/Hot Tub close2Legoland

The single-story home features a welcoming entrance surrounded by lush green landscaping. A private pool is visible through a screened enclosure, furnished with blue lounge chairs. Nearby, an expansive view of the golf course highlights the area’s natural beauty, complemented by an inviting dining and living space indoors.

4.86 out of 5 average rating, 77 reviews

Quiet house with pool on a Top golf course

5 out of 5 average rating, 6 reviews

Home in Davenport

355 Luxury House | Patio | GameRoom | Pool | Grill

A screened-in pool area features a vibrant pool surrounded by greenery. A comfortable seating arrangement is offered, alongside a grill for outdoor cooking. The pool floats in a sunny yellow design while golf course views are visible in the background.