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2026-06-08
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Vacation Rentals in Kissimmee

Sunny Retreat-Colorful Home Pool Great Location

Carey Palm Circle 1602, Kissimmee, United States View map

**Welcome to Sunny Retreat-Colorful Home Pool Great Location**, a vibrant sanctuary nestled just 32 kilometers from the enchanting Kissimmee. This delightful haven offers a perfect blend of serenity… More

From US$ 328 Book Now

Upstay Family Home W Resort Access & Private Pool

2973 Banana Palm Drive, Kissimmee, United States View map

**Upstay Family Home W Resort Access & Private Pool** offers an idyllic retreat in the sunny heart of Florida, just 34 km from the vibrant city of Kissimmee. This enchanting premises combines the… More

From US$ 149 Book Now

5 Mi To Wdw! Spacious Resort Escape W/ Pool Access

2704 Club Cortile Cir, Kissimmee, United States View map

5 Mi To Wdw! Spacious Resort Escape With Pool Access Kissimmee villa is merely a 6-minute walk from the Sam's Club, offering guests to unwind at a Jacuzzi. More

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Margaritavilla At Emerald Island

8611 Sunrise Key Drive, Kissimmee, United States View map

**Welcome to Margaritavilla at Emerald Island, Kissimmee** With convenient access to grocery stores like Wal-Mart and major thoroughfares, everything you need is within easy reach. More

From US$ 246 Book Now

Kid-Approved Stay Pool, Parks & Themed Rooms!

4444 Le Reve Court, Kissimmee, United States View map

Located just 8 minutes' walk from Give Kids The World Village Resort, the 4-bedroom Kid-Approved Stay Pool, Parks & Themed Rooms! Kissimmee villa offers a private pool for guests to relax by. More

From US$ 232 Book Now

Spacious 3Br In Reunion Resort - Minutes From Disney!

7770 Sandy Ridge Drive Building 29. Apt 122, Kissimmee, United States View map

The 3-room Spacious 3Br In Reunion Resort - Minutes From Disney! Kissimmee is located in Kissimmee, approximately a 10-minute drive from Mystic Dunes Golf Club, and offers guests an outdoor swimming… More

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Palm Tree Paradise Cottage Near Disney With Margaritaville Resort & Island H20 Waterpark Access - 3087Pi

3087 Pirate Way, Kissimmee, United States View map

The traditional Palm Tree Paradise Cottage Near Disney With Margaritaville Resort & Island H20 Waterpark Access - 3087Pi Kissimmee is located a 10-minute ride from Orange Lake Legends and invites… More

From US$ 391 Book Now

Tranquil Retreat - Serene Getaway

Challenge Drive 1240, Kissimmee, United States View map

Welcome to Tranquil Retreat - Serene Getaway, where the picturesque charm of Kissimmee meets luxurious comfort. Nestled just 28 kilometers from the vibrant heart of Kissimmee, this exquisite getaway… More

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Solara Resort Relaxing Oasis,Pool,Waterpark,By Disney

1614 Carey Palm Cir, Kissimmee, Fl 34747, Usa, Kissimmee, United States View map

Solara is a tranquil retreat that embodies relaxation and luxury, situated just a short 60-minute drive from the excitement of Kissimmee. Nestled away from the hustle and bustle, this serene oasis is… More

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2605 Pawnall

2605 Pawnall Street, Kissimmee, United States View map

Situated in the enchanting town of Celebration, known for its close ties to Walt Disney Company, 2605 Pawnall provides an exceptional base for your Disney adventures, just a stone's throw from the… More

From US$ 424 Book Now

Sea Mist Retreat

2028 Fleming Mist Place, Kissimmee, United States View map

Welcome to the Sea Mist Retreat, an enchanting escape nestled just 32 kilometers from the vibrant heart of Kissimmee and approximately 50 kilometers from the bustling Orlando International Airport. More

From US$ 625 Book Now

Themed Villa With Private Pool Games Massage Chair

8857 Candy Palm Road, Kissimmee, United States View map

Located in the West Kissimmee district of Kissimmee and just 6 minutes' walk from the Paradise Palms Boulevard|the Paradise Palms Resort, Themed Villa With Private Pool Games Massage Chair Kissimmee… More

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3131-102Jj Storey Lake, Condo 2/2 Lake View

3131 Paradox Cir #102, Kissimmee, United States View map

**Nestled in the heart of Kissimmee, the 3131-102Jj Storey Lake, Condo 2/2 Lake View offers a serene getaway that balances comfort and convenience.** This charming retreat is located just 12 km from… More

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Mickey'S Magical Townhome Venetian Bay Villages

4005 San Sabastian Drive, #103 Building 53, Kissimmee, Fl 34741, Kissimmee, United States View map

**Welcome to Mickey's Magical Townhome Venetian Bay Villages** Nestled just 6 kilometers from the vibrant heart of Kissimmee, Mickey's Magical Townhome Venetian Bay Villages offers a perfect blend of… More

From US$ 436 Book Now

Amazing 8Br W Pool Theater Game Room By Disney

2936 Penelope Loop, Kissimmee, United States View map

Experience the epitome of luxury and fun at the Amazing 8Br W Pool Theater Game Room By Disney, nestled just 10 kilometers from the enchanting attractions of Kissimmee. This magnificent residence… More

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Awesome 9 Br-10 Min To Disney W Game & Theme Rooms

1864 Caribbean View Terrace, Kissimmee, United States View map

**Welcome to Awesome 9 Br-10 Min To Disney W Game & Theme Rooms**, a sprawling escape designed for both thrill-seekers and leisure travelers. Just 10 minutes away from the enchanting world of Disney,… More

From US$ 445 Book Now

The Hidden Gem Cottage

962 Savanna Drive, Kissimmee, United States View map

**Discover the Enchantment of The Hidden Gem Cottage** Nestled just 13 kilometers from the vibrant town of Kissimmee, The Hidden Gem Cottage offers guests a quintessential Floridian escape. More

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Prime Locale - Vacation Paradise

Clock Tower Drive 4853, Kissimmee, United States View map

**Experience Unmatched Comfort at Prime Locale - Vacation Paradise** Welcome to Prime Locale - Vacation Paradise, your ideal retreat just 12 kilometers from the charming streets of Kissimmee. More

From US$ 239 Book Now

Spacious 4Br Townhome W Pool -Free Bbq

1828 Tropical Palms Circle, Kissimmee, United States View map

**Welcome to Spacious 4Br Townhome with Pool & Free BBQ** Ideally situated, the Spacious 4Br Townhome is just 50 km from Orlando International Airport, making travel a breeze. More

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Luxury 3Br Condo Near Disney With Pool

3163 Britannia Boulevard D, Kissimmee, United States View map

If you want to stay in the West Kissimmee district of Kissimmee, the spacious 126 m² Luxury 3Br Condo Near Disney With Pool Kissimmee is a good choice located, 4.8 km from Mystic Dunes Golf Club at… More

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Casa 4Q Lucaya Com Temas Disney E Clubhouse

2941 Lucayan Harbour Circle, Kissimmee, United States View map

Situated within 25 minutes' walk of local amusement parks, the 3-bedroom Casa 4Q Lucaya Com Temas Disney E Clubhouse Kissimmee includes an outdoor swimming pool, as well as a Jacuzzi and hot public… More

From US$ 212 Book Now

Family Paradise Villa • Bbq • Pool • Close To Disney

1517 Mumbai Wy, Kissimmee, Fl 34747, Hoa Ky, Kissimmee, United States View map

Situated around 25 minutes' walk from the Rum Run, the 6-bedroom Family Paradise Villa • Bbq • Pool • Close To Disney Kissimmee provides access to numerous tourist attractions in the area. Located in… More

From US$ 353 Book Now

Resort Home, Pool, Spa, Game Near Disney-New!

8953 Amelia Downs Trail, Kissimmee, United States View map

**Welcome to Your Perfect Getaway** Nestled just 32 kilometers from the vibrant heart of Kissimmee, Resort Home, Pool, Spa, Game Near Disney-New! More

From US$ 794 Book Now

Your Happy Place At Tuscana Resort

8020 Tuscany Way 2103, Kissimmee, United States View map

In the enchanting surroundings of Kissimmee, Your Happy Place At Tuscana Resort offers an idyllic retreat for travelers seeking comfort combined with adventure. This delightful air-conditioned… More

From US$ 200 Book Now

5 Bedrooms 4 Bathrooms Indian Creek 8056 Sd

8056 Santee Drive, Kissimmee, United States View map

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From US$ 626 Book Now

Luxury Villa Near Disney And Universal

Tranquil Trail, Kissimmee, United States View map

Discover the ultimate getaway experience at the Luxury Villa Near Disney And Universal, a stunning retreat just 35 km from the vibrant city of Kissimmee. This exquisite accommodation combines luxury… More

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2974 Viscount Villa 3Bed+ Pool&Spa

2974 Viscount Circle, Kissimmee, United States View map

Welcome to the 2974 Viscount Villa 3Bed+ Pool&Spa, a luxurious retreat located just a short drive from the bustling entertainment hubs of Kissimmee and Orlando. With its elegant design and modern… More

From US$ 187 Book Now

Extended Pool Deck - South Facing - Pool & Spa - Game Room - Family Friendly - Nr Disney

9002 Murano Mews Court, Kissimmee, United States View map

Featuring horseback riding to make your visit more entertaining, the 4-bedroom Extended Pool Deck - South Facing - Pool & Spa - Game Room - Family Friendly - Nr Disney Kissimmee villa is 3.8 km from… More

From US$ 320 Book Now

Kissimmee Condo: Community Perks, 10 Mi To Disney!

2221 San Vittorino Cir Unit 101, Kissimmee, United States View map

Located a mere 9 minutes' stroll from the Fun 'n Wheels Family Fun Parks, the 3-bedroom Kissimmee Condo Community Perks, 10 Mi To Disney! villa comes with an indoor swimming pool, a Jacuzzi and an… More

From US$ 89 Book Now

Bahama Bay Resort 04402

Kissimmee, United States View map

Positioned in the serene West Kissimmee district, Bahama Bay Resort 04402 offers a tranquil escape just 33 km from the vibrant heart of Kissimmee. Accessible via Orlando International Airport… More

From US$ 87 Book Now

Contemporary Condo With Pool Table, Rooftop Terrace And Large Loft With Reunion Resort Water Wark Access Near Disney At Spectrum Resort Orlando By Rentyl - B40 #224

7760 Sandy Ridge Drive B40 #224, Kissimmee, United States View map

Nestled in the heart of Kissimmee, the Contemporary Condo offers a perfect blend of luxury and convenience, making it an ideal retreat for families and groups seeking a memorable getaway. Just 23 km… More

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Orlando 1Br Relaxing Condo Next To Disney With Pool View

5565 West Irlo Bronson Memorial Highway W330, Kissimmee, United States View map

**Welcome to the Orlando 1Br Relaxing Condo Next To Disney With Pool View**, an ideal retreat for families and couples looking to explore the magic of Orlando. Located just 14 km from the enchanting… More

From US$ 176 Book Now

Harry Potter - 4Bd Sleep 10 Pool, Spa And E-Bbq! Solara Resort

1775 Sawyer Palm Place, Kissimmee, United States View map

The 4-bedroom Harry Potter - 4Bd Sleep 10 Pool, Spa And E-Bbq! Solara Resort Kissimmee villa is located nearly a 25-minute walk from Northeast Regional City Park and provides billiards for active… More

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Townhouse C/Piscina Priv. Perto Da Disney

2661 Reading Trail, Kissimmee, United States View map

The 3-bedroom Townhouse C/Piscina Priv. Perto Da Disney Kissimmee villa is nestled just 1.2 km from the Pioneer Village at Shingle Creek and provides a hot tub. More

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1840 Caribbean View

1840 Caribbean View Terrace, Kissimmee, United States View map

Set just 3.5 km from the vibrant heart of Kissimmee, 1840 Caribbean View is a tropical oasis that beautifully combines comfort and luxury. This exquisite villa offers a welcoming retreat just a… More

From US$ 358 Book Now

Smooth Sailing Cottage With Private Pool Near Disney And Margaritaville Resort & Island H20 Waterpark Access - 7992Sh

7992 Shaker Street, Kissimmee, United States View map

Nestled in the Disney World district of Orlando, the 4-bedroom Smooth Sailing Cottage With Private Pool Near Disney And Margaritaville Resort & Island H20 Waterpark Access - 7992Sh Kissimmee is 2.5… More

From US$ 649 Book Now

Waterpark & Heated Pool 20Min To Disney

8885 Qin Loop, Kissimmee, United States View map

The 6-bedroom Waterpark & Heated Pool 20Min To Disney Kissimmee villa entices active guests with access to a fitness room and is located around a 10-minute ride from Highlands Reserve GC. Featuring a… More

From US$ 743 Book Now

9203 Sommerset Hills Drive

9203 Sommerset Hills Drive, Kissimmee, United States View map

**Welcome to Sommerset Hills**, a serene retreat nestled just 29 kilometers from the vibrant city of Kissimmee. Offering a perfect blend of modern comfort and elegant charm, this exquisite property… More

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Beautiful & Spacious 3-Bed Condo Champions Gate

Splash Shot Place 1095, Kissimmee, United States View map

Experience a splendid getaway at the Beautiful & Spacious 3-Bed Condo Champions Gate, located just 29 km from the vibrant heart of Kissimmee and a convenient 50 km from Orlando International Airport.… More

From US$ 192 Book Now

South Facing Private Pool With Lake View & Spa - Quiet Vacation Area - Family Friendly

2424 Hybrid Drive, Kissimmee, United States View map

Staying at the 2-bedroom South Facing Private Pool With Lake View & Spa - Quiet Vacation Area - Family Friendly Kissimmee villa, guests can easily reach the Green Barn on the Lake, located around 4… More

From US$ 269 Book Now

Third Floor Unit In Bahama Bay

114 Lucaya Loop, Kissimmee, United States View map

**Welcome to the Third Floor Unit in Bahama Bay Villa**, a splendid retreat that combines comfort and convenience in the heart of Kissimmee. Situated just an hour's drive from the vibrant energy of… More

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3Br Resort Pool Jacuzzi Minutes To Disney 4730

4730 Terra Esmeralda Drive, Kissimmee, United States View map

Offering a Jacuzzi for a relaxing experience, 3Br Resort Pool Jacuzzi Minutes To Disney 4730 Kissimmee villa is located 10 minutes' drive from Medieval Times Dinner & Tournament. Located 4.3 km from… More

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7Bdm Prvt Pool Villa - Gated Resort 10Min To Disney

8591 Sunrise Key Drive, Kissimmee, United States View map

Positioned within a gated resort, the exquisite 7Bdm Prvt Pool Villa - Gated Resort 10Min To Disney offers an idyllic retreat just 10 minutes away from the magical allure of Disney. This elegantly… More

From US$ 339 Book Now

Bright & Cheery Decor, Townhome Wspashpool-3015Pp

8971 Candy Palm Road,, Kissimmee, United States View map

Located in the West Kissimmee district, the 3-bedroom Bright & Cheery Decor, Townhome Wspashpool-3015Pp Kissimmee villa is about a 25-minute walk from the Rum Run and offers a Jacuzzi. More

From US$ 187 Book Now

Pool House 4Br Near Disney Shops

4902 Windermere Ave, Kissimmee, United States View map

Accommodating up to 12 guests, the 4-bedroom Private Pool 4Br Home In Orlando Kissimmee is situated 4.8 km from renowned cultural sites such as the Osceola County Welcome Center and History Museum. More

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Ever After Estate

8554 La Isla Drive, Kissimmee, United States View map

Ever After Estate Kissimmee villa is located about 10 minutes by car from Mighty Jungle Golf, giving access to various tourist spots nearby. More

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Apartment In Reunion Resort ¡Near To Disney

Heritage Crossing Court 1597, Kissimmee, United States View map

**Experience Luxury and Convenience at Reunion Resort Near Disney** Conveniently situated, Apartment In Reunion Resort ¡Near To Disney boasts easy access to Orlando's famous theme parks… More

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Themed House W Disney Rooms Private Pool & Spa

Leader Street 969, Kissimmee, United States View map

Located 3.2 km from Highlands Reserve Boulevard, the 5-bedroom Themed House W Disney Rooms Private Pool & Spa Kissimmee villa gives access to various tourist sites in the vicinity. More

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Excitement Getaway Oasis

7603 Excitement Drive, Kissimmee, United States View map

Situated only 1.8 km from Arnold Palmer Golf Course, the 6-bedroom Excitement Getaway Oasis Villa Kissimmee includes a swimming pool, as well as a hot tub to relax in. Featuring access to a terrace… More

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Castle On Hillcrest- 9 Miles To Disney!

119 Hillcrest Rd, Kissimmee, United States View map

Located around 25 minutes' walk from Highlands Reserve Boulevard, Castle On Hillcrest- 9 Miles To Disney! Kissimmee villa comes with a private swimming pool equipped with a patio. Featuring a patio… More

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