Upstay Vacation Rentals in Orlando - Florida
155 properties available
Get ready for a fun-filled Florida escape at this 5-bedroom, 4-bathroom villa in the exciting Windsor Cay Resort! With themed kids’ bedrooms, a Mario Bros–inspired game room, and a private pool, this spacious home is perfect for families and groups looking for comfort, entertainment, and resort-style living—just 8 miles from Walt Disney World!Relax
Big Home, Bigger Fun! Bring the whole crew to this spacious 10-bedroom, 8-bathroom retreat in the Bella Vida Resort—just 5 miles from Walt Disney World! With themed kids' rooms, a private pool and hot tub, game zones galore, and room for up to 18 guests, it’s made for unforgettable family vacations or group getaways.Outdoor Oasis & Backyard Bliss:•
Kick back and relax at this modern 5-bedroom, 6-bathroom villa located in the exclusive Encore Resort community. Designed for families and group stays, the home spans two spacious stories with multiple lounging areas, a private backyard oasis, and comfort-first amenities throughout.Outdoor fun, all day long:• Private pool & hot tub with pool safety
Magical Memories Start Here! This vibrant 5-bedroom, 4.5-bathroom getaway in Windsor Cay Resort is a dream come true for families and Disney fans alike. With themed kids’ rooms, a private pool, game room, and access to resort-style amenities, it’s the perfect launchpad for your next Orlando adventure.From lazy days by the pool to movie nights and m
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
Sun, Fun & Space for Everyone! This vibrant 7-bedroom, 5-bathroom retreat at ChampionsGate Resort is tailor-made for large families and group getaways. With a private pool, movie loft, in-home arcade, and room for up to 23 guests, this stay blends resort perks with all the comforts of home—just 15–20 minutes from Orlando’s top attractions.Whether y
Located just off Highway 192, this pet-friendly 3-bedroom, 2-bathroom condo offers comfort, space, and easy access to restaurants, golf, shopping, and top Orlando attractions. With stylish interiors and resort-style amenities, it's the perfect getaway for families or groups—just minutes from the action.Comfortable & Family-Ready• 3 spacious bedroom
Welcome to your perfect Orlando getaway—a bright, pet-friendly 2-bedroom, 2-bathroom condo designed for comfort, connection, and convenience. Tucked beside a tranquil nature reserve and just a short drive from world-famous attractions like Walt Disney World and Universal Studios, this 1,288 sq.ft retreat delivers resort-style relaxation with all th
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
Your Private Outdoor Escape• Exclusive private pool and spillover hot tub• Comfortable outdoor lounge seating and sofa for up to 6 guests• Expansive patio space• Pool safety fence for added peace of mind• Ambient outdoor lighting• Peaceful, quiet-street residential settingRelax, Gather, and Feel at Home Indoors• Spacious open-concept living area• C
Home Features:· 10 bedrooms, 8 bathrooms· Smart TVs in every bedroom and both the living room and upstairs lounge· Modern, fully equipped chef's kitchen with new stainless steel appliances· Granite countertop island with bar-stool seating· Monopoly themed games room with table tennis, foosball and air-hockey· In-home movie theatre· In-home Washer &
Soak up the Florida sunshine at this private group getaway in Sonoma Resort! Your outdoor oasis features a private swimming pool, spill-over hot tub, sun loungers, and a covered dining area with a BBQ grill — perfect for long afternoons and fun-filled evenings under the stars.Private Patio Perks:• Screened-in swimming pool with added privacy panels
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