Holiday rentals with a pool in Kissimmee

Pool Spa + Outdoor Entertainment | Golf Retreat

Escape to a one-of-a-kind golf retreat in Davenport, where resort-style outdoor living meets family-friendly entertainment. Spend your days relaxing by the private pool & spa, enjoying movies on the outdoor TV, and challenging the family in the Super Mario game room, all just minutes from Disney Whether you're planning a family vacation, golf getaway, or long weekend with friends, this beautifully renovated 4-bedroom home was designed for connection, comfort, and unforgettable Florida memories.

Luxury Villa! /Game Room/ Pool Heater

Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and overflow Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

Villa Resort Club

VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

Near Disney | Heated Pool, King Bed, Arcade

✨ Family-Friendly Retreat Near Disney in a gated, safe & quiet community 🏰 Loved by guests for its cleanliness, comfort, and fast communication. 🏊‍♂️ Unwind after park days in your private HEATED pool 🍔 Enjoy the outdoor BBQ for easy family meals 🎮 Have fun in the upgraded game room with pool table, ping pong, foosball, and a retro arcade ⭐ Hosted by 3 experienced Superhosts known for quick, reliable replies. A perfect balance of fun and relaxation. Book now as dates fill fast!

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

Welcome to Sol Oasis Cove! This amazing pool / spa cottage has one bedroom on the first floor and 2 bedrooms upstairs with a balcony positioned perfect for the sunset over the lake! This property comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater.

10 Min to Disney | Kings | Heated Pool | Games

✨ Perfect family getaway just minutes from Disney magic! ✨ This spacious 4-bedroom home sleeps 9 and features 2 king beds, 4 full beds, and 1 twin, plus fun Mickey Mouse & Minion themed rooms kids love. Unwind in your private screened pool, enjoy the game room with arcade games, ping pong, foosball & pool table, or relax with cozy board-game nights. 🏰 Animal Kingdom 10 mins Epcot & Hollywood Studios 15 mins Book now and start making unforgettable family memories!

Luxury Encore Pool Spa Pets Game Rm Theater Gym

Amazing Brand New Modern Luxurious Home at Encore Resort Reunion. PET-FRIENDLY & Minutes to all Theme Parks. BRAND NEW HOME. Private Pool & Spa / Game Room / Movie Theater / Gym / Massage Chair / Fireplace / PS5 / Board Games & Much More. Embrace the extraordinary and book your stay at our home, where luxury, entertainment come together for an unforgettable vacation experience. ** Please review the rules before booking. Waterpark access is not included. **

Orlando Dream Escape | Private Pool | Disney

Welcome to your perfect Orlando getaway! Enjoy this beautifully renovated home with a private pool, just 20 minutes from Disney, Universal, and SeaWorld. Perfect for families and groups of up to 8 guests. Features 3 bedrooms, 2 full bathrooms, a fully equipped kitchen, fast Wi-Fi, washer & dryer, free parking, and self check-in. Relax, unwind, and create unforgettable memories close to Orlando’s best attractions, shopping, and restaurants. 🏊‍♀️ Private Pool

4BR Disney & Universal Themed Villa Reunion Resort

Welcome to our newly remodeled 4BR/4BA luxury villa in Reunion, designed for families and groups seeking comfort, style, and a magical Orlando escape. Enjoy brand-new furnishings, modern finishes, Toy Story and Mickey themed bedrooms, a spacious open living area with massage chair, and a fully equipped game room featuring air hockey, arcade basketball, and PlayStation. Relax in your private screened pool with optional heating after unforgettable park days.

Amazing 8Bdrms-5Bath/Game room/Pool

The Space * Accommodates: 22 * Bedrooms: 8 * Bathrooms: 5 * Property type: Luxury House * Location: Storey Lake * 12 miles from Magic Kingdom * 10 miles from Animal Kingdom * 16 miles from Universal Studios * 2.4 miles from Lake Buena Vista Factory Stores (Outlet) * 4 miles from The Loop (Outlet) * 22 miles from MCO * Located close to Highways 192 and 535, the property is located close to the main restaurants, pharmacies, markets.

Montego Bay Retreat | 15 Min to Disney

Enjoy a stylish stay in this newly renovated 3-bedroom, 2-bath home, perfect for families and groups of up to 9 guests. Located only 15 minutes (8 miles) from Disney and close to Orlando’s top attractions, restaurants, and shopping. Relax in modern, comfortable spaces after a fun day at the parks. Outdoor grill available for $30/day (gas included). The perfect mix of location, comfort, and convenience for your Florida vacation! ✨

Luxe Family Retreat | Pool Villa Near Disney & MCO

Escape to this beautifully designed family retreat featuring a private screened pool, BBQ gazebo, foosball table, spacious open-concept living areas, and a fully equipped kitchen. Ideally located near Disney, MCO Airport, outlets, shopping, restaurants, and Orlando’s top attractions. Perfect for family vacations, group trips, or a relaxing getaway with all the comforts of home.