Upstay Inc

(7 rentals)
Upstay Inc
We get it - travel needs have changed big time. You want a vibe, a neighborhood, a space that feels like home but without the hassle, and that's where we come in.

Since 2019, we’ve manage hundreds of vacation properties, in 4 different countries, and you can expect best-in-class hospitality from us. Before you arrive we’ll email you all you need to know, ...
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We get it - travel needs have changed big time. You want a vibe, a neighborhood, a space that feels like home but without the hassle, and that's where we come in.

Since 2019, we’ve manage hundreds of vacation properties, in 4 different countries, and you can expect best-in-class hospitality from us. Before you arrive we’ll email you all you need to know, and our team is here for you day or night, with 24/7 support.

Welcome to Upstay.
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Kissimmee House
15 BR | 15 BA | Sleeps 36 | Quick View
Sleeps 36, 15 bedrooms, 15 bathrooms

$1085

avg/night

$1,085
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

This vacation home isn't just a place to stay; it's your own personal wonderland. Step outside, and you'll be greeted by a backyard oasis that dreams are made of – a sparkling swimming pool with a spillover jacuzzi hot tub and a sun-soaked sundeck, complete with lounging chairs that ...

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Property Type

Kissimmee House

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Kissimmee House
12 BR | 11.5 BA | Sleeps 24 | Quick View
Sleeps 24, 12 bedrooms, 11.5 bathrooms

$530

avg/night

$530
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Nestled over at the Bella Vida Resort, just a measly 5 miles away from the magical kingdom of Walt Disney World (yeah, we're basically neighbors!), this 12 bedroom mansion is big enough to host 24 of your favourite people.Let's kick things off with the amazing back deck. Picture this: a ...

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Property Type

Kissimmee House

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Davenport House
8 BR | 5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 5 bathrooms

$228

avg/night

$228
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

The back patio faces a garden view, giving you the benefit of extra privacy without any rear facing neighbours! Enjoy soaking up the Florida sunshine on one of the sun loungers, or kick back and relax in the shade under the covered outdoor lounge area. Feeling peckish? You can add BBQ to your menu since ...

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Property Type

Davenport House

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Kissimmee House
15 BR | 16 BA | Sleeps 33 | Quick View
Sleeps 33, 15 bedrooms, 16 bathrooms

$330

avg/night

$330
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

The whole crew will love the swimming pool. It has a spill-over jacuzzi hot tub and a spacious sundeck with lounge chairs. After a swim, why not enjoy a poolside BBQ meal? There's space for 12 guest to dine al fresco. Bring out your inner Gordon Ramsey while cooking on your private grill!Had ...

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Property Type

Kissimmee House

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Kissimmee House
12 BR | 11.5 BA | Sleeps 30 | Quick View
Sleeps 30, 12 bedrooms, 11.5 bathrooms

$516

avg/night

$516
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

At this 30-guest capacity, 12-bedroom mansion, bedtime will be a blast because these kids bedrooms have some of the coolest beds we've ever seen! For all the Star Wars fans, if you've ever wanted to sleep under an AT-AT, this is your time to shine. Whether storming the battle of Hoth or getting ...

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Property Type

Kissimmee House

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Kissimmee House
12 BR | 11 BA | Sleeps 26 | Quick View
Sleeps 26, 12 bedrooms, 11 bathrooms

$390

avg/night

$390
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

From the minute you pull through the gated entry you will be lost in your dream vacation. Located at the beautiful Veranda Palms Resort, this 26 guest capacity vacation home has everything you could possibly need for a fantastic stay.Let's start with the gorgeous sundeck patio at the back of ...

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Property Type

Kissimmee House

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Kissimmee House
10 BR | 8 BA | Sleeps 20 | Quick View
Sleeps 20, 10 bedrooms, 8 bathrooms

$180

avg/night

$180
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

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 · In-home Washer ...

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Property Type

Kissimmee House

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