Villa holiday rentals in Winter Haven

Rest Relax Unwind at Orista Endless Summer Villa

Endless Summer Villa is the perfect vacation destination. With a game room, 4 bedrooms & 4 bathrooms, our villa is handicap accessible and perfect for families. Take a splash in the private pool or relax in one of our two master suites, each outfitted with top-quality furnishings and bedding. Let our beautifully landscaped pool transport you to a tropical paradise, all while being just a short drive away from Disney, SeaWorld, and Universal. Book your stay with Orista Endless Summer Villa today!

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

Make memories to last a lifetime in our luxurious seven-bedroom home (sleeps 21) at Orlando's premier vacation community. Enjoy your own Batman cave game room, private pool (heated at no extra charge*), and hot tub. Our 100% Five-Star rating from previous guests and our generous cancellation policy means you can book with confidence. Only 15 minutes to Disney and a short walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

** New Construction ** Breathtaking view of lake, private dock (2 kayaks for guests included), beach/swim area, outdoor shower, large private balcony w/gas grill and gorgeous sunsets! 2 Bedrooms each w/walk in closet, two full baths, full kitchen w/all amenities. All new furnishings, (3) 4K Smart TV's, FAST free wifi. Gorgeous location, quiet street, private free parking, 2 private entrances. Villa is detached from main house. Near Disney, LegoLand, Bok Tower. WEEKLY & MONTLY DISCOUNTS

Pirate-Themed Villa w/ Pool + Arcades Near Disney

Ahoy, mateys! ⚓ Step into our one-of-a-kind pirate-themed villa minutes from Disney and Universal. From the ship-shape bedrooms to treasure-chest décor, every corner feeds the imagination. After a day at the parks, dive into private pool, play arcade battles, or watch a movie in theatre. 🛏 8 themed bedrooms | 🛁 5 bathrooms 🔑 24/7 self check-in & Superhost service 🏝 Located in a gated resort with playgrounds, splash zone, tennis & pickleball, and more Book now and set sail for memories!

*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.

Villa con piscina

Fabulosa villa de 4 habitaciones ,dos baños, con sala de juegos, BBQ y piscina privada. Completamente equipada para su conveniencia! Lugar céntrico. Solo a minutos de Disney y de los demás parques de atracción. A 3 minutos de Walmart, Publix y restaurantes variados. Venga con su familia y pase unas vacaciones inolvidables!La casa también cuenta con el disfrute de un área adicional en el área ,que tiene una piscina extra,canchas de tenis un parque para niños y rampa para botes y yeskit .

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.

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**

Mickey Fantasia Family Friendly w/accessibility

This home was designed with the idea of imagination in mind. Imagination can take you to places you otherwise could have only dreamt of being in; Walt Disney himself said, "If you can dream it, you can do it". The vibrancy and life that fills this house represents imagination. When you set foot in this house, the real world fades away. Here, life can be a rainbow. People of all abilities are welcome to sing, dance, and have fun here.