Upstay Vacation Rentals in Orlando - Florida
153 properties available
This family-friendly townhouse is the perfect home base for your next getaway, located just 20 minutes from Disney and packed with resort-style amenities. With space for up to six guests, it’s ideal for families or small groups looking for comfort, convenience, and fun all in one place.The home features three bedrooms and three bathrooms, an open-c
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-
Sunshine, Style & Space for the Whole Crew! This bright, pet-friendly 3-bedroom, 2-bathroom condo is the ultimate retreat for families, couples, or friend groups ready to enjoy the best of Central Florida. Located just off Highway 192, you'll be surrounded by great dining, golf, shopping, and top attractions—with full access to amazing resort ameni
Magical Moments, Poolside Fun & Resort Perks! This family-friendly 4-bedroom, 3-bathroom villa is the perfect home base for your next Orlando adventure. With Mickey and Star Wars-themed bedrooms, a private pool, and access to Solana Resort’s top-tier amenities, it’s a stay packed with fun, comfort, and convenience—just minutes from Disney!Your Priv
Spacious 9BR Lakeview Villa with Pool, Hot Tub & Resort Perks Welcome to your ultimate family retreat in sunny Kissimmee—just minutes from Disney! This stylish 9-bedroom, 7-bathroom vacation home comfortably sleeps up to 20 guests and is packed with premium amenities both inside and out. From lake views to a resort-style backyard and a fully upgrad
Pool & Outdoor Living• Private pool with a safety fence, fully enclosed by mesh screens• BBQ grill and outdoor dining area• Comfortable outdoor lounge seating with shaded areasEntertainment & Group Spaces• Game room featuring a pool table, Smart TV, and gaming console• Open-concept main living area with ample seating and a large Smart TV• Second-fl
Bella Vida Resort Spacious 8-Bedroom Family Retreat with Private Pool & Game RoomEscape to your perfect Central Florida getaway—a bright and spacious 8-bedroom, 5-bathroom home just 20 minutes from Walt Disney World and Orlando’s top attractions. Designed to blend fun, comfort, and convenience, this retreat is ideal for unforgettable family reunion
Welcome to your perfect Orlando retreat—proudly presented by Upstay! This 3-bedroom, 2.5-bathroom home is thoughtfully designed for families and groups, offering plenty of space to relax, recharge, and reconnect. Fire up the grill for a backyard BBQ under twinkling patio lights, or kick back after a theme park day in one of the cozy, curated bedroo
Please note the listing photos are only representative imagery, the actual furniture and decorations may varyHome Features:• 3 spacious bedrooms• 2 bathrooms (1 ensuite)• Large luxury private balcony• Private Dining area (seats 4)• Spacious living room• Smart TVs• High speed internet connection• Fully equipped kitchen with new stainless steel appli
Sun, space, and family fun! This bright, pet-friendly three-bedroom, two-bathroom condo is perfectly arranged for up to 7 guests. The layout features a fully equipped kitchen, a comfortable living area, and in-suite laundry. A spacious setup where everyone can fuel up for the Disney magic!Please note the listing photos are only representative image
This beautiful home located at ChampionsGate is perfect for your next Orlando vacation. Big enough for the whole family with its 8 bedrooms and 5 bathrooms, this fantastic house can host up to 22 guests at a time.The private back sundeck is a haven for chilling out on lounge chairs while topping off your tan. Enjoy sizzling burgers on the barbecue,
Sunshine, style, and nonstop fun. This vibrant 4 bedroom, 3 bathroom Florida retreat features a private pool, stylish interiors, and a retro Pac Man themed game room for group entertainment. Located in the sought after Bella Vida Resort, you are minutes from Disney with access to world class amenities.Whether you're splashing in the sun or kicking
Tell us what you're looking for and someone will contact you with available options.