Upstay Vacation Rentals in Orlando - Florida


Properties Available 172 properties available
Home Features:• 3 bedrooms (4 beds in total)• 2 Bathrooms • Primary bedroom includes a soaker tub• Smart TVs• High speed wifi internet• Fully equipped kitchen• Large furnished private patios• In suite laundry machines• Central air conditioning• 1288 sq.ft.Building Features:• Outdoor pool• Game room (ping pong table and mini basketball)• Fitness cen
Upstay Condo w Pool Near Disney
Pet Friendly
$120.00 USD / average per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (40)
Home Features:- 6 Bedrooms (8 beds)- 5.5 Bathrooms - Each bedroom has hardwood floor and its own Smart TV- High speed internet service is available throughout the house- Games Room with air hockey, foosball, pool table and big screen TV- Back patio faces a grassy lush environment - no rear neighbours offer added privacy!- Swimming pool with
Bella Vida House with Pool and Games Near Disney
$120.00 - $933.00 USD / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 12 guests
Relax, Connect & Enjoy• Kick back on the group couch with TV entertainment on the ground floor• Gather upstairs on the group couch with TV entertainment• Enjoy shared meals in the dining area with a table setup for 6• Cook favorite meals in the fully equipped kitchen with a convenient kitchen counterRest Easy, Room by Room• Bedroom 1: King-size bed
Vacation Home Near Disney with Resort Pool Access
Pet Friendly
$105.00 - $364.00 USD / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
A Magical Place to Relax and Enjoy• Private pool with BBQ grill for outdoor dining and relaxation• Outdoor lounge area with beach chairs for relaxing and enjoying fresh air• Indoor living area with Smart TV and WiFi for comfort and entertainmentFeel at Home While You Cook and Dine• Fully equipped kitchen for easy meal preparation• Center island wit
Upstay Modern Home Near Disney with Pool
$116.00 - $861.00 USD / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 9 guests
Welcome to your newly renovated Orlando getaway—bright, clean, and designed for comfort after a day of theme parks, shopping, or golf. This modern 1-bedroom suite is located inside a resort-style hotel building in the Sand Lake area, just a short drive to Walt Disney World, Universal Studios, and all the best restaurants and outlets Orlando is know
Newly Renovated Suite with Hot Tub and Pool
$47.00 - $148.00 USD / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
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
Windsor at Westside Resort Home w Pool Hot Tub
Pet Friendly
$245.00 USD / average per night
Bedrooms 8 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 5 (7)
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 parkingBuilding Amenities:• Outdoor pool• Game room (table tennis and mini basketball)• Fitness center• Sauna• Meeting RoomsThis pet-
Upstay Tropical Style Family Condo w Pool
Pet Friendly
$60.00 - $323.00 USD / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to your perfect Orlando base—a bright and spacious 3-bedroom, 2-bathroom condo designed with families and small groups in mind. Whether you're relaxing after a theme park day or enjoying a quiet morning on the balcony, this home has everything you need.Please note the listing photos are only representative imagery, the actual furniture and
Upstay Stylish Resort Getaway w Pool near Disney
Pet Friendly
$115.00 USD / average per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Your Private Poolside Retreat• Private pool for soaking up the Florida sun• BBQ grill for family cookouts• Outdoor dining table for 4, perfect for al fresco meals• Screened patio, a shaded spot to unwind poolsideWhere the Magic Unwinds• Open-concept living area for the whole group to gather together• Central air conditioning and heating for year-ro
Disney Area Villa w Private Pool Resort Access
$86.00 - $579.00 USD / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 11 guests
Shared Spaces for Quality Time• Unwind together on the ground-floor living area couch with TV entertainment• Gather upstairs on the additional living area couch for more group downtime and TV entertainment• Enjoy shared meals in the dining area with a table setup for 6• Cook favorite meals in the fully equipped kitchen with a convenient kitchen cou
Family Home Near Disney w Pool Spa Pool Table
Pet Friendly
$105.00 - $461.00 USD / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Spacious 2-bedroom, 2-bathroom condo with a fully equipped kitchen, private bedrooms, screened-in patio, and resort amenities.Please note the listing photos are only representative imagery, the actual furniture and decorations may varyYour Private Escape Includes:• 2 bedrooms with 1 king bed and 2 queen beds (sleeps 6 guests)• 2 full bathrooms incl
Modern Escape with Private Patio Spa Tub Pool
Pet Friendly
$60.00 - $258.00 USD / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Family-owned and professionally managed by Upstay, Waypoint Villa delivers hotel-quality standards, local support, and a seamless stay from booking to checkout.• Pool Heating ( available October - March )• Hot tub heating ( Available all year- round )• Baby travel essentials available• Thoughtfully designed for groups, no surprise add-onsHome Hi
Upstay Pool Hot Tub Heating Epic Games Room
Pet Friendly
$321.00 USD / average per night
Bedrooms 7 bedrooms
Bathrooms 5 baths
Guests 20 guests
Rating 5 (15)

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