We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Villa vacation rentals in Osceola County

Find and book unique villas on Airbnb

Top-rated villa rentals in Osceola County

Guests agree: these villas are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

A private pool area features a turquoise swimming pool and a spa, both enclosed by a screened lanai. Comfortable seating options include several lounge chairs and a propane grill is available nearby, creating an inviting space for relaxation and outdoor dining.

Villa in Davenport

4.9 out of 5 average rating, 21 reviews

$99May So fac'g pool,spa,lovely,utd,grill pets 242

This 4 bdrm, 3 bath villa is perfect for a family vacation! It sleeps 8 in 4 bedrooms plus a sleeper sofa, private pool and spa. It's walking distance to the community amenities- a gym, a walk in pool, cabanas for shade, a hot tub, a play ground, volleyball court, and a basketball goal! Located in a dedicated wetlands it gives the best of both worlds. The resort is close to shopping and restaurants, yet serene. Go to the parks or play at home! Grill out or eat out! You will want to stay in FL!

Top guest favorite

A sprawling resort-style pool area is highlighted, featuring a large lagoon pool surrounded by seating options under shaded umbrellas. Water slides and a splash pad are visible in the background, along with lush landscaping and palm trees enhancing the vibrant atmosphere.

Villa in Kissimmee

5 out of 5 average rating, 5 reviews

Gated|3m to Disney|Pool & Spa|FREE Resort Access

NEW TO MARKET!!! "Summer House" at Windsor Hills is an extra clean vacation home - recently upgraded with new floors, paint, decor, furniture and brand new Stearns & Foster mattresses in every room. The villa is a 4 Bedroom 4 Bathroom Ensuite property with an attached bathroom on every bedroom! The property has a private pool & hot tub, smart TV's in every room, a game room with a pool table, foosballs table, Smart Tv, 4 leather reclining movie theatre chairs with more space to spread out. Stun

Top guest favorite

The villa features a distinct architectural style with a terracotta roof and a landscaped front yard. Lush palm trees are positioned around the entrance, while a spacious driveway leads to a three-car garage, all set against a tranquil evening sky.

Villa in Kissimmee

5 out of 5 average rating, 106 reviews

Villa Sol Peaceful Pool/Hot tub Home

Close to all major attractions, and airport sits this private villa. It has a little something for all ages! Your family can play in the pool or relax in the hot tub. Enjoy fun game nights with the cabinet full of games, or play a little game of basketball right outside the pool. Enjoy the tennis courts, and playground. Stay in shape while you travel just steps away from the clubhouse gym. There is everything for the beach trips or the ball games. All of your baby's needs are covered as well.

A screened pool area is visible featuring a private pool and adjoining spa. The clear blue water reflects sunlight, while surrounding greenery adds a touch of nature. The enclosure provides safety and a barrier from the outside, offering a relaxing atmosphere.

Villa in Kissimmee

4.83 out of 5 average rating, 71 reviews

Home w/ PVT Pool, Game Room & Resort access

Our luxurious 5-bedroom, 5.5-bathroom home boasts a spacious living room with Smart TV, a fully-equipped kitchen and dining room, a cozy upstairs living area perfect for movie nights as well as an air-conditioned game room featuring a pool table and air hockey. Venture to the backyard to find even more amazing features such as a spacious private pool and SPA, sun loungers, a barbecue and a table with 6 seats where you and your guests will be able to enjoy some sun-filled al fresco dining.

The image showcases a private pool area encased in a screened enclosure, with a clear blue pool reflecting sunlight. Surrounding the pool are comfortable lounge chairs and a dining table set on a spacious deck, with greenery visible beyond the enclosure.

Villa in Kissimmee

4.91 out of 5 average rating, 55 reviews

Disney Pool Home Kissimmee

Located in the beautiful Crescent Lakes of Kissimmee. Just minutes (12 miles) to Disney. Our 3 Bed, 2 full bath Villa will be sure to make your vacation enjoyable. Relax under the sun or the stars in the south/west facing pool. Lounge and dine on the oversized pool deck. 3 bed, 2 full bath Villa. Community has finishing ponds - catch and release policy. No swimming - we have gators Tennis court, basketball court, football/soccer field with baseball base. Playground and outdoor work out

The image showcases a collage of four distinct spaces. A bright children's bedroom features pink walls adorned with Disney Princess graphics. A themed room with a cosmic design includes multiple spacious beds. An outdoor area highlights a private pool surrounded by lounge chairs. A game room is equipped with a pool table and arcade games, illuminated with vibrant lighting.

Villa in Davenport

4.71 out of 5 average rating, 45 reviews

Free Pool Heat! Themed Rooms|Game Room|Lazy River

Enjoy your stay at this spacious, family-friendly home! MINUTES to Walt Disney World, golf courses and outlet shopping. Beautiful themed interior, and enough space to entertain throughout. This impeccable 9 bedroom, 5 bath home sleeps up to 24. • 🎢 LAZY RIVER and WATER SLIDES • 🌟THEMED Bedrooms • 🌟GAME ROOM •🍴 Stocked Kitchen • 🏖️ Private patio with HEATED POOL • 🛏️ Memory foam mattresses • 📶 High Speed Wi-Fi • 🚼 Pack n play & kids high-chair (1) •👮‍♀️ Gated community

A spacious outdoor area features a sleek pool with a spillover spa, surrounded by laid-back lounge chairs. A dining set with vibrant red chairs and a rustic wooden table accommodates gatherings, while palm trees enhance the setting against a backdrop of the golf course and blue sky.

Villa in Osceola County

5 out of 5 average rating, 6 reviews

Villa Brandivor - New 4 bedroom home with pool

Welcome to Villa Brandivor! Located on the Arnold Palmer Golf Course at the prestigious Reunion Resort, this luxurious villa can accommodate up to 10 guests. This villa features a fully equipped kitchen with stainless steel appliances, a large pool with a spillover spa, Golf Course View, and much more for you and your family to have the best time ever! In addition, the resort is located close to the best tourist attractions and local activities! -2 night minimum.

A private screened patio features a heated swimming pool and a Jacuzzi surrounded by a spacious deck. Outdoor seating is provided, with a dining table and lounge chairs positioned for relaxation. Sunlight glimmers on the water, creating a serene atmosphere.

Villa in Davenport

4.91 out of 5 average rating, 101 reviews

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi

Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

A vibrant collage presents the inviting exterior of Villa Marie, featuring a colorful water playground with slides and a lazy river. A large smart TV is also shown, indicating entertainment options. The image is accented by a promotional banner highlighting free pool heating and BBQ amenities.

Villa in Kissimmee

4.91 out of 5 average rating, 43 reviews

Discover Magic & Elegance at Villa Marie!

As you step inside this freshly renovated 9-bedroom, 6-bathroom villa, you are immediately embraced by a blend of contemporary design and homely warmth. One of the highlights of this residence is its captivating themed rooms. Whether it's the Disney princess realm for the little dreamer or the Marvel superhero sanctuary for the young-at-heart, every room promises an unforgettable journey into the realms of imagination.

A modern living area features a mix of seating options, including a blue sofa and an orange-accented couch, arranged around a dark wooden coffee table. A colorful artwork hangs on the wall, enhancing the vibrant atmosphere. The open layout connects to the kitchen area.

Villa in Kissimmee

4.88 out of 5 average rating, 117 reviews

Wonderful Villa at Storey lake Resort 6 Rooms Pool

Welcome to our luxurious and stunning vacation home located at STOREY LAKE RESORT, taking you on an adventurous journey filled with endless memories and exceptional selfies. We are 15 minutes from Disney and 2 minutes from Target, 5 minutes from Walmart and several other restaurants. All rooms have television and not to mention the private pool. Make some memories in this unique and familiar place.

A modern kitchen area features a large dark countertop with tall wooden chairs positioned around it. Stainless steel appliances and a range hood are visible. Natural light fills the space through a high window, illuminating the adjacent living area furnished with a sofa.

Villa in Kissimmee

4.76 out of 5 average rating, 93 reviews

3bd/4 ba Magic Village Yards | 5 mins to Disney

The Gorgeous Magic Village Yards! Beautifully furnished modern 3BR/4BA townhome w/private hot tub & outdoor BBQ, just 5–6 mins from Disney. 2 king beds + 2 twin beds, each BR has an en suite (1 BA downstairs). COMPARE OUR PRICES TO BOOKING DIRECT AT MAGIC VILLAGE YARDS—THE RESORT CHARGES PER ROOM - ABOUT 3–5X MORE!! Free parking & Wi-Fi. Resort pool & gym available for optional fee. OPTIONAL

A modern two-story villa features a clean exterior with a light color palette. Palm trees frame the entrance, which is accentuated by two outdoor chairs and a welcoming doorway. A spacious garage is visible, complemented by a manicured lawn and clear blue skies.

Villa in Kissimmee

4.78 out of 5 average rating, 9 reviews

3841 Stylish Villa 7BQ Pool and Game Room

Come to Orlando and stay in this lovely villa, specially thought and designed to give guests the feeling of being at home away from home. Fully equipped with the most pleasant and stylish furniture and decorations, stay in this villa comfortably, accommodating all your family and friends for the most complete experience possible on your trip, whether for work or vacation!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Osceola County villa rentals

Free parking on premises

Air conditioning

Private villa rentals

A light-filled living area showcases a white sofa adorned with decorative cushions in blue tones. An elegant round blue ottoman sits at the center on a patterned rug. A large mirror reflects natural light from the window, framed by navy curtains, with decorative elements adding style.

Villa in Davenport

4.84 out of 5 average rating, 86 reviews

5bedroom,pool,18min to Disney, Kissimmee davenport

A spacious outdoor area features a private pool enclosed by a screen, with sunlight streaming onto the water. Inside, a cozy bedroom is highlighted by a wooden headboard and ceiling fan. The kitchen showcases modern appliances and bright cabinetry, contributing to an inviting atmosphere.

Villa in Kissimmee

4.67 out of 5 average rating, 3 reviews

Spacious Villa at 5-Star Resort - Mi from Disney

Top guest favorite

The image showcases a vibrant gaming area with a glowing dance floor, a relaxing outdoor space featuring lounge chairs near the pool, a themed sleeping area with bunk beds, and a foosball table positioned in a cozy game room filled with colorful lighting.

Villa in Davenport

4.98 out of 5 average rating, 43 reviews

6 BD/4.5 Ba Sleeps 14! Lily Pad At Solterra Resort

A well-appointed bedroom features a king-sized bed with pastel-colored bedding and an assortment of decorative pillows. A large window, dressed with light curtains, illuminates the space. A stylish bench at the foot of the bed complements the contemporary decor, while a wall-mounted TV adds modern convenience.

Villa in Kissimmee

4.9 out of 5 average rating, 21 reviews

6BR/4.5BA DisneyVilla,Pool+Spa,Game Room,Clubhouse

The two-story vacation home features a welcoming exterior with a warm yellow facade and a red-tiled roof. Lush greenery lines the driveway, which leads to a spacious garage with a single door. Arched entrances add architectural interest, complemented by decorative features.

Villa in Davenport

4.73 out of 5 average rating, 15 reviews

Luxury Wellness Villa - Private Spa & Pool

A vibrant water attraction features a person surfing on a flow rider wave, creating splashes around them. Surrounding the image are glimpses of a spacious vacation home, showcasing the inviting facade, a covered pool area, and a modern kitchen with dark cabinetry and light countertops.

Villa in Kissimmee

4.83 out of 5 average rating, 69 reviews

Luxury 9Beds Villas With Pool Spa In Solara

The villa exterior showcases a charming pink façade with a landscaped front yard. Two large windows invite natural light, and a palm tree stands beside the entrance. The driveway leads to a single-car garage, framed by well-maintained greenery.

Villa in Davenport

4.73 out of 5 average rating, 56 reviews

Private Villa with Pool near Disney

A private screened lanai features an inviting pool and hot tub surrounded by lounge chairs. A game room is seen with a pool table, seating areas, and colorful wall decor. Bedrooms are present, including a nursery with themed decor and shared spaces for relaxation.

Villa in Kissimmee

4.92 out of 5 average rating, 108 reviews

33 Disney Villa Game Room Movie Theater Pool

Luxury villa rentals

A spacious dining area features a long glass table surrounded by white chairs, set for a large meal with blue and gold accents. A striking blue wall with geometric gold patterns creates a modern backdrop, while contemporary light fixtures illuminate the space.

Villa in Davenport

4.93 out of 5 average rating, 96 reviews

Blue Paradise-15 Bdrms, Sleeps 32-Theater, GameRm

Top guest favorite

A game room showcases vibrant wall art featuring popular characters, equipped with a foosball table and gaming stations. An outdoor pool area displays a slide leading into the pool, bordered by colorful lounge chairs. A themed children's bedroom emphasizes a bunk bed design, while another features cozy bedding with a whimsical backdrop.

Villa in Davenport

4.98 out of 5 average rating, 101 reviews

Pickleball PoolsideMovies |WalkToWaterpark| Arcade

Top guest favorite

A private pool area is illuminated in a soft green hue, surrounded by a screened enclosure. Comfortable lounge chairs are positioned nearby, with a table set under an umbrella. String lights create a warm ambiance as the evening sky darkens.

Villa in Davenport

4.99 out of 5 average rating, 122 reviews

Magical Disney House-Pool & Hot Tub,Free Waterpark

Top guest favorite

A private pool is framed by a stone patio, with lounge chairs positioned nearby for relaxation. Lush greenery and palm trees surround the area, creating a serene outdoor environment. A spa is positioned next to the pool, providing an inviting space for relaxation.

Villa in Four Corners

5 out of 5 average rating, 87 reviews

The Golden Bear Villa | Private Pool & Theater

A vibrant game room is filled with colorful artwork featuring iconic video game characters. Various gaming stations are set up with large screens and controllers. A pool table and foosball table provide additional entertainment options, all set against a bright green floor.

Villa in Kissimmee

4.96 out of 5 average rating, 23 reviews

Luxury 9Bdrm at Solara/Pool/GameRoom

An outdoor area showcases a private pool surrounded by sun loungers, with views of a golf course in the background. The pool's rippling water reflects the clear sky, complementing the serene atmosphere.

Villa in Four Corners

5 out of 5 average rating, 9 reviews

Amazing New Villa! Well Maintained! Fun for all!

Top guest favorite

A private pool features a spacious deck and a whimsical swan float. Adjacent is a covered dining area with views of landscaped grounds. Inside, a kids’ tube slide and superhero-themed decor are seen, along with a game area featuring a billiards table and arcade console.

Villa in Osceola County

4.99 out of 5 average rating, 115 reviews

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

A collage showcasing distinct areas of the villa. The top left features a themed bedroom with ocean decor and multicolored bedding. The top right displays a spacious sleeping area with aquatic-themed walls. The bottom left highlights a plush seating area in a private cinema, while the bottom right illustrates a castle-themed bunk bed area for children.

Villa in Kissimmee

4.76 out of 5 average rating, 17 reviews

Stunning 12BR Lake View Luxury Home Hot Pool & Spa

Villa rentals with a pool

Villa in Davenport

4.74 out of 5 average rating, 43 reviews

Fabulous 4 Bedroom Villa with private pool

The living area features a dark leather sofa adorned with decorative pillows, complemented by a glass side table and a coffee table. Wooden dining chairs surround a rectangular table, with an adjacent open-concept kitchen visible in the background. Natural light filters through decorative windows.

Villa in Kissimmee

4.81 out of 5 average rating, 57 reviews

NEAR DISNEY 3 bdrm villa with pools and clubhouse!

Villa in Kissimmee

4.91 out of 5 average rating, 100 reviews

Luxurious Pool Villa, Minutes From Disney World

A screened-in area surrounds the heated in-ground pool, offering a secure and inviting space. Two lounge chairs are positioned poolside, providing a place to relax. Sunlight filters through the enclosure, highlighting the clear water and greenery beyond the surrounding fence.

Villa in Kissimmee

4.81 out of 5 average rating, 231 reviews

Veranda Palms Luxurious Home w/Pool & NEAR DISNEY

Villa in Kissimmee

5 out of 5 average rating, 7 reviews

Mickey’s Backyard 6Bedroom Villa Resort- BBQ&Pool

Villa in Kissimmee

4.8 out of 5 average rating, 5 reviews

Spacious Villa w/ Private Heated Pool & Office

A screened-in patio area features a private pool surrounded by comfortable lounge chairs. The inviting water reflects the colors of the sunset sky, and a small dining table is visible nearby. The home is designed for relaxation and outdoor enjoyment.

Villa in Davenport

4.92 out of 5 average rating, 155 reviews

Beautiful 4 Bedroom Pool Villa Near Disney World

A resort-style pool is framed by palm trees, featuring clear turquoise water. The spacious clubhouse, with a distinctive architectural style, is visible in the background, characterized by a large entryway and a welcoming facade. Green shrubs are neatly arranged around the pool area.

Villa in Kissimmee

4.91 out of 5 average rating, 137 reviews

Famous Windsor Palms Resort Pool Home Next2 Disney

Destinations to explore