Upstay Vacation Rentals in Orlando - Florida
152 properties available
Your dream group getaway starts here! This 10-bedroom, 8.5-bathroom villa at Windsor Cay Resort is designed for large families and groups up to 26 guests seeking fun, comfort, and style—all just 9 miles from Disney and under an hour from Universal. Step inside to discover stunning themed bedrooms, vibrant entertainment spaces, and modern amenities
Theme-Packed 12-Bedroom Family Retreat with Pool, Theatre & Resort Access – Sleeps 30!Ready for the ultimate group getaway? This 12-bedroom, 11.5-bathroom home at Bella Vida Resort is bursting with themed kids’ rooms, entertainment for all ages, and resort-style perks — all just 20 minutes from Walt Disney World.Whether you’re sleeping under an AT-
Sun, space & style! This 4-bedroom, 3-bathroom Crystal Cove Resort home is perfect for families and small groups, with a private pool, spacious patio, and access to resort amenities — all just 6 miles from Disney and 11 miles from Universal.Soak up the sun on your private patio oasis:• Private swimming pool with private fenced yard & garden views•
Settle into this inviting 3-bedroom, 2-bath townhouse in the gated Lucaya Village Resort, where home comfort meets resort convenience. With space for up to 8 guests, it’s an ideal choice for families, friends, or small groups looking to stay close to the magic while enjoying plenty of room to relax.What You’ll Love:• 3 bedrooms | 4 beds | 2 bathroo
Create Magical MemoriesAfter a day at Disney, unwind in a space designed for fun and connection• Private pool for adults to relax• Hot tub for extra relaxation• BBQ grill, sun loungers, and dining area for outdoor funGather, Dine, and ConnectEnjoy shared meals and family time in a space designed for connection• Fully equipped kitchen with center is
Movie Lounge, Games & Poolside Fun – Minutes from Disney!Make unforgettable memories in this newly updated 6-bedroom, 5.5-bath Solana Resort home—perfect for family vacations, group getaways, and theme park adventures. With a private pool, hot tub, movie lounge, and game-filled garage, this spacious retreat offers entertainment for every guest, jus
Home Features:- 8 bedrooms, 5 bathrooms - Fun themed bedrooms: A Star Wars-themed bunk room and a Taylor Swift-themed twin room- Private swimming pool and hot tub- Furnished patio with covered outdoor dining area and sun loungers- In-home Harry Potter themed movie theater- Additional 2 TV lounge areas with smart TVs- Large capacity indoor dining ta
Spacious, stylish, and perfect for families—this 3-bedroom, 2-bathroom condo offers everything you need for a fun and relaxing Orlando stay. With a private screened-in balcony, fully equipped kitchen, and access to resort-style amenities, this pet-friendly suite is your ideal home base just off Hwy 192.Indoor Comforts:• Bedroom 1: King bed + Smart
Your dream group getaway starts here! This spacious 8-bedroom, 6-bathroom home sleeps up to 16 guests and delivers fun at every turn — with a private pool, bubbling hot tub, game room, and even a home theater. Located in the sought-after Windsor at Westside Resort, you’ll enjoy luxury living, resort perks, and a prime location just minutes from Dis
Suite Features:• 3 bedrooms (4 beds in total) • 2 Bathrooms • Complimentary wifi• Smart TVs • Fully equipped kitchen• In suite laundry machines• Central air conditioning• Large furnished private balcony• Free onsite parking• Pet-friendly (One pet is welcome for a $99 fee)Building Amenities:• Outdoor pool• Game room (table tennis and mini basketbal
Features two levels with a private pool, hot tub, BBQ grill, immersive themed bedrooms, and home theater.Outdoor Living:• Private swimming pool & hot tub with LED lighting for evening ambiance• Pool safety fence & outdoor seating• Patio dining area with umbrella• Pool loungers and outdoor lightingEntertainment & Relaxation:• Garage converted privat
Unit Features:• 3 bedrooms (4 beds in total)• The kids will love the Mickey themed bunk bed room!• 2 Bathrooms including an ensuite bathroom - with soaker tub• Smart TVs• High speed internet• Fully equipped kitchen• Central air conditioning• In suite laundry machines• Private furnished patios• 1288 sq.ft.• Free onsite parking Welcome to your perfe
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