
Holiday houses in Osceola County
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Top-rated holiday rentals in Osceola County
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The Sun-Kissed Retreat / near Disney
Welcome to your Orlando retreat! This spacious 5-bedroom, 4.5-bathroom townhome at the exclusive Azur Resort offers everything you need for an unforgettable vacation. Designed with comfort and style in mind, this home is ideal for families, groups, and anyone looking to explore the magic of Orlando. Located just mins from Orlando's top attractions- Disney World, Universal, and world-class shopping and dining. You’re at the center of it all! Book now and start making memories at the Azur Resort!

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema
The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

3BR / 2BR Heated Pool Home 7 Min to Disney |
✨ Experience comfort, style, and a private heated pool 💦 (optional) just 7 minutes from Disney World! This 3BR/2BA Kissimmee home is perfectly located near theme parks, shopping, and dining — and designed for families looking to unwind in a sparkling-clean, beautifully curated space. 📍Prime Kissimmee Location ⭐7 Min– Walt Disney World ⭐5 min–Orlando Premium Outlets ⭐15 min – Universal Studios, SeaWorld, Epic Universe 🎢 ⭐ 25 min – MCO Airport ✈️ ⭐ Walk to Walmart, Publix & Starbucks ☕️

Getaway w/ Game Room + Pvt Pool | Solara
Welcome to our single-family home inside the prestigious Solara Resort in Orlando, the perfect getaway for families and friends seeking both comfort and excitement. This spacious 5-bedroom, 4.5-bathroom retreat features modern décor, a fully equipped kitchen, a cozy living and dining area, and a private pool with SPA for endless fun under the Florida sun. Guests will also enjoy a game room in the garage and a stylish loft with TV, making it an ideal spot to relax after a day at the parks.

Lake View, South Pool, Spa & Game Room Fun!
• Spacious 6BR, 2-story home | Sleeps 12 • Private screened pool with relaxing spa (South-west) • Fully enclosed pool deck with loungers & outdoor dining for 8 • Fun-filled games room with pool table, foosball & arcade games • Two separate living spaces – perfect for families & groups • Open-plan main floor with modern, fully equipped kitchen • Large family dining table plus casual breakfast area • Smart TVs in every bedroom & living area • 🎁 Complimentary welcome pack of goodies o

Quiet house with pool on a Top golf course
Cozy home surrounded by nature and one of the best golf courses in Florida. "Consistently Ranked Among the Nation's Best!" If you are vacationing in Orlando and want to play golf, you cannot pass up the opportunity to play one of the best golf courses in Orlando, Florida. located close to Disney and Legoland, you also have close to Walmart, Win Dixie, fast food places and much more. Also do not miss the opportunity to try the southern dunes restaurant with very affordable prices.

TreeHouse in the Cloud, (Close toTheme Parks
The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Pool House in a Quiet Area, Disney Universal
Relax with the whole family at this peaceful place to stay. Fully renovated, spacious, Modern 3BD 2BA Pool home on more than 2 acres in Saint Cloud. Just moments away from the Florida turnpike and highway 192 by vehicle, easy access to theme parks, water parks, airport. Grocery stores, shopping and dining are just moments from home. Fully Secured with fence, gate lock, main door smart lock, security cameras etc. Smart TVs in all Bedrooms and Family room.

Lakeside Crooked Lake Cottage
Wake up to beautiful sunrises on the lake in this beautiful 2 bd 1 & 1/2 bath cottage.Bring your boat, poles, food and clothes. Relax on your porch facing the water or even on the small beach located just feet from your door. Crooked Lake is a State registered Outstanding waterway and is one of the largest lakes in Polk county with avg. depths of 20 ft- 50 ft. You can find a large variety of fish here that include catfish, bluegill, speck

Beautiful off-grid tiny home cottage #3
Retreat to the food covered grounds of this off-grid oasis in Central Florida, reconnect to the beauty and vibrancy of nature, and experience the magnitude of freedom and abundance it has to offer on your sustainable getaway. Your shipping container has a full kitchen, mini-split cooler and spacious shower with an on-demand water heater fed by pristine well water... you would never know you're off-grid!

3 Bedrooms/ 2.5 Bathrooms At Reunion! (7635)
• Resort: Reunion • 3 Bedrooms/2.5 Bathrooms/Sleeps 10 • Disney (15 min) Sea World (20 min) Universal (25 min) • Convention Center (25 min) Legoland (40 min) • Location: Heritage Crossing Way, Kissimmee FL 34747

NEW Stuning 09 Bedroom/LED At Pool/ Solara Resort
The Space • Accommodates: 22 • Bedrooms: 9 • Bathrooms: 6 • Property type: Luxury Villa • Location: Solara Resort
Popular amenities for Osceola County holiday rentals
Other great holiday rentals in Osceola County

Epic Villa Near Disney w Arcade, Theater, Spa Pool

Kissimmee Condo w/ Perks: 6 Mi to Disney World!

Reunion Resort, Amazing Views, Pool / Spa!

Cozy Windsor Palms Condo - Your Orlando Gateway!

Fun & Luxury: Home & Water Park Included

Dream Cozy 3BR Condo - Disney 5 Min, Walk to Pool!

Park To Park Paradise LLC

Vacay Villa
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Give Kids the World Village
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Sebastian Inlet
- Playalinda Beach
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club




