Upstay: Bright Family-Friendly Retreat with Patio — Kissimmee, FL — vacation rental

Upstay: Bright Family-Friendly Retreat with Patio

Nightly
📍 Kissimmee, FL, US
GGuesty$166
Per night · ~ estimatesHow we estimate

Whether it’s a family trip, group escape, or friends’ reunion, this stylish 3-bedroom, 2.5-bath home—presented by Upstay—is designed for connection and comfort. Whip up meals in the chef-ready kitchen, lounge under patio string lights, or relax in open-concept living spaces. With warm vibes and a group-friendly layout, it’s more than just a stay—it’s where your next best memories begin. Book your stay now!

About the Home

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 bedrooms. From movie nights to memory-making meals, this home is your launchpad for unforgettable Orlando moments. Soak Up the Sunshine or Fire up the Grill: • Private outdoor patio lounge with outdoor seating and string lighting • BBQ grill with propane provided on arrival • Spacious driveway and garage—parking for up to 4 cars (2 in driveway + 2 in garage) Feast, Lounge & Gather: • Fully equipped kitchen with stainless steel appliances & ample counter space • Indoor dining area for shared meals and memory-making • Smart TV (42") and high-speed Wi-Fi for movie nights and binge sessions • Dedicated laptop-friendly workspace under the stairs Dream Big, Sleep Easy: Sleeps up to 8 guests across 3 well-appointed bedrooms • Bedroom 1 (Main Floor): King bed + crib | Ensuite bath with shower, tub & bidet • Bedroom 2 (Second Floor): Queen bed • Bedroom 3 (Second Floor): 2 Twin beds • Half bathroom on main floor, full bath upstairs with tub/shower & bidet We've Got All of Your Comforts Covered: • Central air conditioning • Garage laundry area with dryer Unbeatable Location: • Walt Disney World Resort ~ 8 miles • SeaWorld Orlando ~ 13 miles • Universal Studios ~ 17 miles • Orlando International Airport (MCO) ~ 18 miles Why Stay With Us? We’re experts at delivering unforgettable group getaways. Our homes are clean, spacious, and full of personality — from custom designs to immersive entertainment spaces. We handle the details, so you can focus on fun. This isn’t just a stay — it’s your group’s next great adventure. Book today!

Good to know

• For a smooth and secure check-in experience, all guests may be required to complete ID and Enso Boarding Pass verification before arrival. Check-in instructions will be shared once verification is completed. Thank you for helping us ensure a seamless stay! • Please note that the second twin bed in Bedroom 3 is a pull-out bed. • Please note that pool service is scheduled weekly and may occur during your stay. It’s a brief visit to keep the pool clean, and technicians will only access the pool area. Thank you for your understanding. • The pool is located at the entrance to the condominium, it is 10mins walking Additional Services: • BBQ propane tank: 69 USD (one-time fee) • Pack ’n Play rental: 39 USD (one-time fee) • Highchair rental: 29 USD (one-time fee) • Mid-stay cleaning available for stays over 3 nights (additional fee, advance booking required)

The Neighborhood

Nestled in the quiet and family-friendly Chatham Park community, this home offers the perfect balance of comfort and convenience. Located just minutes from the vibrant heart of Kissimmee, Chatham Park is a well-maintained residential neighborhood known for its peaceful atmosphere, scenic walking trails, and proximity to major Orlando attractions. Whether you're heading to Disney World, exploring local parks, or enjoying nearby shopping and dining at The Loop or Old Town, you’ll find everything within easy reach. The neighborhood also features community amenities like a pool, playgrounds, and green spaces—perfect for travelers looking for a relaxing home base close to the action.

Guest Access

• Guest will have full access to the entire property during their stay. • There is driveway and garage parking for up to 4 cars (2 in driveway + 2 in garage) (Please do not park on the grass or block sidewalks, fire hydrants, or other driveways)

House Rules and Terms

1. Parties, events and smoking/vaping of any kind are prohibited in or around our property and risk a fine of $150 and/or your full deposit will be forfeited. 2. Please check-out on time. Late departures will result in a fine of $150 for each additional hour the property cannot be accessed for turnover. 3. Large messes will result in an additional cleaning fee. Please clean up after yourselves. 4. Outside of service animals, pets are not permitted at this property. Any evidence of pets will result in a fine and/or forfeiture of your full deposit. 5. Firearms and weapons are strictly prohibited on the property. • If any of these house rules are broken, you and your group may be subject to additional charges or be requested to vacate the property immediately without refund.

What this place offers

Safety & cleaning 7Family, pets & fun 3Parking & access 4Views & setting 2Tech & work 5Pool & outdoors 4Kitchen & dining 14Comfort & essentials 18Rules & details 1
Carbon monoxide detector
Cleaning Disinfection
Cleaning before checkout
Enhanced cleaning practices
Fire extinguisher
High touch surfaces disinfected
Smoke detector
Family/kid friendly
Suitable for children (2-12 years)
Suitable for infants (under 2 years)
Free parking on premises
Free parking on street
Garage
Private entrance
Downtown
Town
Desk
Internet
Laptop friendly workspace
TV
Wireless Internet
BBQ grill
Garden or backyard
Outdoor seating (furniture)
Patio or balcony
Baking sheet
Blender
Coffee maker
Dining table
Dishes and silverware
Dishwasher
Freezer
Kitchen
Microwave
Oven
Refrigerator
Stove
Toaster
Wine glasses
Air conditioning
Bathtub
Bed linens
Body soap
Ceiling fan
Clothing storage
Conditioner
Dryer
Essentials
Hair dryer
Hangers
Heating
Hot water
Iron
Room-darkening shades
Shampoo
Shower gel
Towels provided
Long term stays allowed

Booking and price

Book on
the host's own site (upstayreservation.guestybookings.com). CielStay links you there and charges no fee.
Nightly rate
Below the typical rate for the 740 homes we list in Kissimmee

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Explore around Kissimmee

Kissimmee & the Orlando Theme Park Area, Florida
Travel guide · Florida
Kissimmee & the Orlando Theme Park Area, Florida
Kissimmee and the surrounding Orlando area communities — Davenport, ChampionsGate, and south Orlando — form the heartland of American family vacation travel. Walt Disney World, Universal Orlando, and SeaWorld anchor a destination where multi-bedroom villas with private heated pools, themed bedrooms, and resort-community water parks have become the defining accommodation. Whether your group wants a six-bedroom villa with a game room five minutes from Disney, an eight-bedroom resort estate with twin theaters at ChampionsGate, or a condo near International Drive, this guide covers where to stay, what to expect from the resort communities, and how to plan a trip centered on the world's most famous concentration of theme parks.

Property sourced from Guesty • Listing stale? Update it!

$166/ night
GuestsUp to 8
Bedrooms3
Bathrooms2.5
Guests2
Pets · not listed as allowed0
📅 No current calendar from the host's site
GGuesty$166
Per night · ~ estimatesHow we estimate