Vacation Rentals
254 properties available
Pool Days, BBQs & Outdoor Fun• Private screened pool for refreshing swims and family fun• Poolside lounge area with wall mounted TV for outdoor relaxation• BBQ grill for backyard cookouts• Outdoor dining table for al fresco mealsFamily Time Starts Here• Spacious open concept living room with Smart TV• Fully equipped kitchen with stainless steel app
Upstay Family Home w Private Pool Resort Access
$100.00 - $440.00 USD / per night
5
bedrooms
6
baths
10
guests
Relax, Unwind & Play:• Private outdoor pool with lounge seating• Shaded patio + BBQ grill for al fresco meals• Indoor & outdoor dining areas – perfect for group meals• Game room with shuffleboard, pool table & arcade games• In-home movie theater for private screenings• High-speed WiFi & Smart TVs• Central air conditioning & heating• In-home laundry
Upstay Family Home w Cinema Pool BBQ Clermont
$220.00 USD / average per night
5
bedrooms
4
baths
12
guests
5
(15)
Resort Living, Private Poolside Bliss & Endless Family Fun! This spacious 5-bedroom, 5-bathroom retreat is your ticket to a perfect Florida vacation. Set in a stunning resort community with two luxury clubhouses, this home features a private pool, Jacuzzi hot tub, themed entertainment spaces, and top-tier amenities for the whole crew—just minutes f
Upstay Resort Home w Private Pool Near Disney
$184.00 USD / average per night
4
bedrooms
3
baths
8
guests
5
(122)
Welcome to A3 Lapa Living – your chic coastal escape in the heart of Jacó. This stylish third-floor walk-up (stairs only) is the perfect retreat for couples, friends, or a small family looking to stay close to the action while enjoying modern comfort.Step into a bright, sunlit space with an open-concept layout. Whip up meals in the fully equipped k
Upstay Modern Jac Beach Getaway with Pool Access
$102.00 USD / average per night
2
bedrooms
2
baths
6
guests
5
(27)
Backyard games, bold design, and big Austin vibes—this 4-bedroom, 3-bathroom Eastside stunner is purpose-built for epic group trips, family reunions, and weekends where the only plan is to make memories.Sprawling across a spacious, open-concept layout with room for up to 12 guests, this home strikes the perfect balance between a playful entertainme
Mini Golf Fireplace East Austin Group Retreat
$554.00 USD / average per night
4
bedrooms
3
baths
12
guests
5
(26)
Welcome to Enchanted Garden Resort – Where Comfort Meets Elegance 🌿✨Property Highlights: Spacious split-level, three-story townhomes 🏡 Designed to blend modern elegance with everyday functionality 4 bedrooms and 3.5 bathrooms – perfect for families or group stays 🛏️🛁Bedroom Configuration: Master Bedroom: Queen-size bed 👸· Private
4BR Enchanted Home Resort Pool Family Comfort
$95.00 - $372.00 USD / per night
4
bedrooms
3
baths
8
guests
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
Upstay Pet friendly Condo with Pool near Disney
$115.00 USD / average per night
3
bedrooms
2
baths
6
guests
5
(20)
Outdoor Entertaining• Private pool with hot tub and safety net• Beach loungers• BBQ grillComforts of Home• Lounge area with smart TV and Roku for guest entertainment• A fully equipped kitchen for large groups• Large 8-seat dining table with additional kitchen counter seats• Central air conditioning and heating• Second upstairs living area designed
Upstay Luxury Home with Pool Hot Tub Games Room
$140.00 - $954.00 USD / per night
5
bedrooms
2
baths
16
guests
Suite Features:• 3 bedrooms• 2 Bathrooms • Complimentary wifi• Smart TVs • Fully equipped chef's kitchen• In suite laundry machines• Central air conditioning• Large private balcony• Free onsite parkingBuilding Amenities:• Outdoor pool• Game room (table tennis and mini basketball)• Fitness center• Sauna • Meeting RoomsThis pet-friendly three-bedroom
Upstay Condo Near Disney w Pool Sauna
$105.00 USD / average per night
3
bedrooms
2
baths
6
guests
5
(48)
Welcome to your ultimate family retreat in ChampionsGate! This stunning 9-bedroom, 5-bathroom vacation home is built to host large groups (up to 26 guests) in total comfort and entertainment. With vibrant themed bedrooms, a private pool and hot tub, a full arcade-style games room, and a private in-home movie theater, there’s something for everyone
Upstay Villa Sleeps 26 Theater Arcade Pool
$375.00 USD / average per night
9
bedrooms
5
baths
26
guests
5
(8)
Gather, Dine & Relax• Relax on the group couch in the living area with TV entertainment• Enjoy shared meals in the dining area with seating for 6• Prepare meals in the fully equipped kitchenSettle In & Unwind• Master Bedroom: Queen-size bed · Private en-suite bathroom• Bedroom 2: Queen-size bed · Private en-suite bathroom• Bedroom 3: Full-size bed
Family Vacation Home Near Disney with Resort Pool
$95.00 - $371.00 USD / per night
4
bedrooms
3
baths
8
guests
Gather, Dine & Cook• Relax in the open-concept living area with comfortable seating and TV entertainment• Enjoy shared meals in the dining area• Prepare favorite meals in the fully equipped kitchen with granite countertops• Cook with high-end stainless steel appliancesSleep, Unwind & Recharge• Master Bedroom: King-size bed with private en-suite bat
Magical Townhome Near Disney w Resort Pool Access
$105.00 - $546.00 USD / per night
4
bedrooms
3
baths
8
guests
Tell us what you're looking for and someone will contact you with available options.
Copyright © 2026 • Upstay
All Rights Reserved.