Upstay — Vacation Rentals

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219 of 219 listings

Upstay Spacious 5BR Villa Private Pool and Hot Tub — photo 1

Upstay Spacious 5BR Villa Private Pool and Hot Tub — photo 2

Upstay Spacious 5BR Villa Private Pool and Hot Tub — photo 3

Upstay Spacious 5BR Villa Private Pool and Hot Tub — photo 4

Upstay Spacious 5BR Villa Private Pool and Hot Tub — photo 5

Upstay Spacious 5BR Villa Private Pool and Hot Tub

Kissimmee, Florida

5 bedrooms · 9 beds · 5.5 bathrooms

From$238/ night

Upstay Resort Home w private pool—ChampionsGate — photo 1

Upstay Resort Home w private pool—ChampionsGate — photo 2

Upstay Resort Home w private pool—ChampionsGate — photo 3

Upstay Resort Home w private pool—ChampionsGate — photo 4

Upstay Resort Home w private pool—ChampionsGate — photo 5

Upstay Resort Home w private pool—ChampionsGate

Davenport, Florida

8 bedrooms · 10 beds · 5 bathrooms

From$225/ night

Upstay: Poolside Mansion w/ Themed Arcade & Cinema — photo 1

Upstay: Poolside Mansion w/ Themed Arcade & Cinema — photo 2

Upstay: Poolside Mansion w/ Themed Arcade & Cinema — photo 3

Upstay: Poolside Mansion w/ Themed Arcade & Cinema — photo 4

Upstay: Poolside Mansion w/ Themed Arcade & Cinema — photo 5

Upstay: Poolside Mansion w/ Themed Arcade & Cinema

Davenport, Florida

6 bedrooms · 9 beds · 5 bathrooms

From$237/ night

Upstay: Family Retreat w Pool, Cinema & Games Room — photo 1

Upstay: Family Retreat w Pool, Cinema & Games Room — photo 2

Upstay: Family Retreat w Pool, Cinema & Games Room — photo 3

Upstay: Family Retreat w Pool, Cinema & Games Room — photo 4

Upstay: Family Retreat w Pool, Cinema & Games Room — photo 5

Upstay: Family Retreat w Pool, Cinema & Games Room

Clermont, Florida

10 bedrooms · 15 beds · 8 bathrooms

From$362/ night

High Rise Condo w Balcony & Breathtaking Views — photo 1

High Rise Condo w Balcony & Breathtaking Views — photo 2

High Rise Condo w Balcony & Breathtaking Views — photo 3

High Rise Condo w Balcony & Breathtaking Views — photo 4

High Rise Condo w Balcony & Breathtaking Views — photo 5

High Rise Condo w Balcony & Breathtaking Views

Kitchener, Canada

1 bedroom · 1 bed · 1 bathroom

FromCA$115/ night

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub — photo 1

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub — photo 2

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub — photo 3

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub — photo 4

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub — photo 5

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub

Kissimmee, Florida

8 bedrooms · 8 beds · 5 bathrooms

From$308/ night

Upstay-Luxury 3BR Home w Private Pool & Games Room — photo 1

Upstay-Luxury 3BR Home w Private Pool & Games Room — photo 2

Upstay-Luxury 3BR Home w Private Pool & Games Room — photo 3

Upstay-Luxury 3BR Home w Private Pool & Games Room — photo 4

Upstay-Luxury 3BR Home w Private Pool & Games Room — photo 5

Upstay-Luxury 3BR Home w Private Pool & Games Room

Clermont, Florida

3 bedrooms · 5 beds · 3 bathrooms

From$125/ night

Stunning Townhome with Private Pool & Games Room — photo 1

Stunning Townhome with Private Pool & Games Room — photo 2

Stunning Townhome with Private Pool & Games Room — photo 3

Stunning Townhome with Private Pool & Games Room — photo 4

Stunning Townhome with Private Pool & Games Room — photo 5

Stunning Townhome with Private Pool & Games Room

Clermont, Florida

3 bedrooms · 5 beds · 3 bathrooms

The Gerrard | Match Day Group Stay w Patio — photo 1

The Gerrard | Match Day Group Stay w Patio — photo 2

The Gerrard | Match Day Group Stay w Patio — photo 3

The Gerrard | Match Day Group Stay w Patio — photo 4

The Gerrard | Match Day Group Stay w Patio — photo 5

The Gerrard | Match Day Group Stay w Patio

Toronto, Canada

2 bedrooms · 2 beds · 2 bathrooms

FromCA$146/ night

Casa Hotels: Elegant 2BR Suite in Leslieville — photo 1

Casa Hotels: Elegant 2BR Suite in Leslieville — photo 2

Casa Hotels: Elegant 2BR Suite in Leslieville — photo 3

Casa Hotels: Elegant 2BR Suite in Leslieville — photo 4

Casa Hotels: Elegant 2BR Suite in Leslieville — photo 5

Casa Hotels: Elegant 2BR Suite in Leslieville

Toronto, Canada

2 bedrooms · 2 beds · 1 bathroom

FromCA$177/ night

Family Condo Near Disney w Pool & Gym—Pets Welcome — photo 1

Family Condo Near Disney w Pool & Gym—Pets Welcome — photo 2

Family Condo Near Disney w Pool & Gym—Pets Welcome — photo 3

Family Condo Near Disney w Pool & Gym—Pets Welcome — photo 4

Family Condo Near Disney w Pool & Gym—Pets Welcome — photo 5

Family Condo Near Disney w Pool & Gym—Pets Welcome

Winter Garden, Florida

3 bedrooms · 4 beds · 2 bathrooms

Upstay Pristine 3BR Home with Private Pool & BBQ — photo 1

Upstay Pristine 3BR Home with Private Pool & BBQ — photo 2

Upstay Pristine 3BR Home with Private Pool & BBQ — photo 3

Upstay Pristine 3BR Home with Private Pool & BBQ — photo 4

Upstay Pristine 3BR Home with Private Pool & BBQ — photo 5

Upstay Pristine 3BR Home with Private Pool & BBQ

Clermont, Florida

3 bedrooms · 6 beds · 3 bathrooms

From$106/ night

Upstay: Crystal Cove Resort Villa w/ Pool & Games — photo 1

Upstay: Crystal Cove Resort Villa w/ Pool & Games — photo 2

Upstay: Crystal Cove Resort Villa w/ Pool & Games — photo 3

Upstay: Crystal Cove Resort Villa w/ Pool & Games — photo 4

Upstay: Crystal Cove Resort Villa w/ Pool & Games — photo 5

Upstay: Crystal Cove Resort Villa w/ Pool & Games

Kissimmee, Florida

4 bedrooms · 5 beds · 3 bathrooms

From$175/ night

The Gerrard | New Unit Near FIFA 2026 — photo 1

The Gerrard | New Unit Near FIFA 2026 — photo 2

The Gerrard | New Unit Near FIFA 2026 — photo 3

The Gerrard | New Unit Near FIFA 2026 — photo 4

The Gerrard | New Unit Near FIFA 2026 — photo 5

The Gerrard | New Unit Near FIFA 2026

Toronto, Canada

2 bedrooms · 2 beds · 2 bathrooms

FromCA$175/ night

Waterfront Family Mansion w BBQ, Games Room & Pool — photo 1

Waterfront Family Mansion w BBQ, Games Room & Pool — photo 2

Waterfront Family Mansion w BBQ, Games Room & Pool — photo 3

Waterfront Family Mansion w BBQ, Games Room & Pool — photo 4

Waterfront Family Mansion w BBQ, Games Room & Pool — photo 5

Waterfront Family Mansion w BBQ, Games Room & Pool

Kissimmee, Florida

8 bedrooms · 10 beds · 5 bathrooms

From$230/ night

Pet-friendly Condo Pool, Sauna—Near Disney — photo 1

Pet-friendly Condo Pool, Sauna—Near Disney — photo 2

Pet-friendly Condo Pool, Sauna—Near Disney — photo 3

Pet-friendly Condo Pool, Sauna—Near Disney — photo 4

Pet-friendly Condo Pool, Sauna—Near Disney — photo 5

Pet-friendly Condo Pool, Sauna—Near Disney

Winter Garden, Florida

3 bedrooms · 4 beds · 2 bathrooms

Upstay Spacious Home w Patio Vista Cay Resort — photo 1

Upstay Spacious Home w Patio Vista Cay Resort — photo 2

Upstay Spacious Home w Patio Vista Cay Resort — photo 3

Upstay Spacious Home w Patio Vista Cay Resort — photo 4

Upstay Spacious Home w Patio Vista Cay Resort — photo 5

Upstay Spacious Home w Patio Vista Cay Resort

Orlando, Florida

3 bedrooms · 8 beds · 2 bathrooms

From$130/ night

The Gerrard | Watch Party Ready Basement — photo 1

The Gerrard | Watch Party Ready Basement — photo 2

The Gerrard | Watch Party Ready Basement — photo 3

The Gerrard | Watch Party Ready Basement — photo 4

The Gerrard | Watch Party Ready Basement — photo 5

The Gerrard | Watch Party Ready Basement

Toronto, Canada

2 bedrooms · 2 beds · 1 bathroom

FromCA$183/ night

Elegant Suite w Patio, BBQ Grill! — photo 1

Elegant Suite w Patio, BBQ Grill! — photo 2

Elegant Suite w Patio, BBQ Grill! — photo 3

Elegant Suite w Patio, BBQ Grill! — photo 4

Elegant Suite w Patio, BBQ Grill! — photo 5

Elegant Suite w Patio, BBQ Grill!

Toronto, Canada

3 bedrooms · 4 beds · 2 bathrooms

FromCA$197/ night

Upstay Condo Near Disney w Pool & Sauna — photo 1

Upstay Condo Near Disney w Pool & Sauna — photo 2

Upstay Condo Near Disney w Pool & Sauna — photo 3

Upstay Condo Near Disney w Pool & Sauna — photo 4

Upstay Condo Near Disney w Pool & Sauna — photo 5

Upstay Condo Near Disney w Pool & Sauna

Winter Garden, Florida

3 bedrooms · 3 beds · 2 bathrooms

Spacious 4BR Family Townhouse—Private Pool & BBQ — photo 1

Spacious 4BR Family Townhouse—Private Pool & BBQ — photo 2

Spacious 4BR Family Townhouse—Private Pool & BBQ — photo 3

Spacious 4BR Family Townhouse—Private Pool & BBQ — photo 4

Spacious 4BR Family Townhouse—Private Pool & BBQ — photo 5

Spacious 4BR Family Townhouse—Private Pool & BBQ

Kissimmee, Florida

4 bedrooms · 5 beds · 3 bathrooms

From$160/ night

Modern 3BR Condo w Private Patio 7min to Disney — photo 1

Modern 3BR Condo w Private Patio 7min to Disney — photo 2

Modern 3BR Condo w Private Patio 7min to Disney — photo 3

Modern 3BR Condo w Private Patio 7min to Disney — photo 4

Modern 3BR Condo w Private Patio 7min to Disney — photo 5

Modern 3BR Condo w Private Patio 7min to Disney

Winter Garden, Florida

3 bedrooms · 4 beds · 2 bathrooms

Modern 3BR Resort Condo with Pool near Disney — photo 1

Modern 3BR Resort Condo with Pool near Disney — photo 2

Modern 3BR Resort Condo with Pool near Disney — photo 3

Modern 3BR Resort Condo with Pool near Disney — photo 4

Modern 3BR Resort Condo with Pool near Disney — photo 5

Modern 3BR Resort Condo with Pool near Disney

Winter Garden, Florida

3 bedrooms · 4 beds · 2 bathrooms

Upstay: Large Resort Home w Private Pool & Hot Tub — photo 1

Upstay: Large Resort Home w Private Pool & Hot Tub — photo 2

Upstay: Large Resort Home w Private Pool & Hot Tub — photo 3

Upstay: Large Resort Home w Private Pool & Hot Tub — photo 4

Upstay: Large Resort Home w Private Pool & Hot Tub — photo 5

Upstay: Large Resort Home w Private Pool & Hot Tub

Kissimmee, Florida

7 bedrooms · 10 beds · 6.5 bathrooms

From$170/ night

Upstay Spacious 5BR Villa Private Pool and Hot Tub — photo 1

Upstay Spacious 5BR Villa Private Pool and Hot Tub — photo 2

Upstay Spacious 5BR Villa Private Pool and Hot Tub — photo 3

Upstay Spacious 5BR Villa Private Pool and Hot Tub — photo 4

Upstay Spacious 5BR Villa Private Pool and Hot Tub — photo 5

Upstay Spacious 5BR Villa Private Pool and Hot Tub

Kissimmee, Florida

5 bedrooms · 9 beds · 5.5 bathrooms

From$238/ night

Upstay Resort Home w private pool—ChampionsGate — photo 1

Upstay Resort Home w private pool—ChampionsGate — photo 2

Upstay Resort Home w private pool—ChampionsGate — photo 3

Upstay Resort Home w private pool—ChampionsGate — photo 4

Upstay Resort Home w private pool—ChampionsGate — photo 5

Upstay Resort Home w private pool—ChampionsGate

Davenport, Florida

8 bedrooms · 10 beds · 5 bathrooms

From$225/ night

Upstay: Poolside Mansion w/ Themed Arcade & Cinema — photo 1

Upstay: Poolside Mansion w/ Themed Arcade & Cinema — photo 2

Upstay: Poolside Mansion w/ Themed Arcade & Cinema — photo 3

Upstay: Poolside Mansion w/ Themed Arcade & Cinema — photo 4

Upstay: Poolside Mansion w/ Themed Arcade & Cinema — photo 5

Upstay: Poolside Mansion w/ Themed Arcade & Cinema

Davenport, Florida

6 bedrooms · 9 beds · 5 bathrooms

From$237/ night

Upstay: Family Retreat w Pool, Cinema & Games Room — photo 1

Upstay: Family Retreat w Pool, Cinema & Games Room — photo 2

Upstay: Family Retreat w Pool, Cinema & Games Room — photo 3

Upstay: Family Retreat w Pool, Cinema & Games Room — photo 4

Upstay: Family Retreat w Pool, Cinema & Games Room — photo 5

Upstay: Family Retreat w Pool, Cinema & Games Room

Clermont, Florida

10 bedrooms · 15 beds · 8 bathrooms

From$362/ night

High Rise Condo w Balcony & Breathtaking Views — photo 1

High Rise Condo w Balcony & Breathtaking Views — photo 2

High Rise Condo w Balcony & Breathtaking Views — photo 3

High Rise Condo w Balcony & Breathtaking Views — photo 4

High Rise Condo w Balcony & Breathtaking Views — photo 5

High Rise Condo w Balcony & Breathtaking Views

Kitchener, Canada

1 bedroom · 1 bed · 1 bathroom

FromCA$115/ night

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub — photo 1

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub — photo 2

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub — photo 3

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub — photo 4

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub — photo 5

Upstay: Ultimate Orlando Retreat w Pool & Hot Tub

Kissimmee, Florida

8 bedrooms · 8 beds · 5 bathrooms

From$308/ night

Upstay-Luxury 3BR Home w Private Pool & Games Room — photo 1

Upstay-Luxury 3BR Home w Private Pool & Games Room — photo 2

Upstay-Luxury 3BR Home w Private Pool & Games Room — photo 3

Upstay-Luxury 3BR Home w Private Pool & Games Room — photo 4

Upstay-Luxury 3BR Home w Private Pool & Games Room — photo 5

Upstay-Luxury 3BR Home w Private Pool & Games Room

Clermont, Florida

3 bedrooms · 5 beds · 3 bathrooms

From$125/ night

Stunning Townhome with Private Pool & Games Room — photo 1

Stunning Townhome with Private Pool & Games Room — photo 2

Stunning Townhome with Private Pool & Games Room — photo 3

Stunning Townhome with Private Pool & Games Room — photo 4

Stunning Townhome with Private Pool & Games Room — photo 5

Stunning Townhome with Private Pool & Games Room

Clermont, Florida

3 bedrooms · 5 beds · 3 bathrooms

The Gerrard | Match Day Group Stay w Patio — photo 1

The Gerrard | Match Day Group Stay w Patio — photo 2

The Gerrard | Match Day Group Stay w Patio — photo 3

The Gerrard | Match Day Group Stay w Patio — photo 4

The Gerrard | Match Day Group Stay w Patio — photo 5

The Gerrard | Match Day Group Stay w Patio

Toronto, Canada

2 bedrooms · 2 beds · 2 bathrooms

FromCA$146/ night

Casa Hotels: Elegant 2BR Suite in Leslieville — photo 1

Casa Hotels: Elegant 2BR Suite in Leslieville — photo 2

Casa Hotels: Elegant 2BR Suite in Leslieville — photo 3

Casa Hotels: Elegant 2BR Suite in Leslieville — photo 4

Casa Hotels: Elegant 2BR Suite in Leslieville — photo 5

Casa Hotels: Elegant 2BR Suite in Leslieville

Toronto, Canada

2 bedrooms · 2 beds · 1 bathroom

FromCA$177/ night

Family Condo Near Disney w Pool & Gym—Pets Welcome — photo 1

Family Condo Near Disney w Pool & Gym—Pets Welcome — photo 2

Family Condo Near Disney w Pool & Gym—Pets Welcome — photo 3

Family Condo Near Disney w Pool & Gym—Pets Welcome — photo 4

Family Condo Near Disney w Pool & Gym—Pets Welcome — photo 5

Family Condo Near Disney w Pool & Gym—Pets Welcome

Winter Garden, Florida

3 bedrooms · 4 beds · 2 bathrooms

Upstay Pristine 3BR Home with Private Pool & BBQ — photo 1

Upstay Pristine 3BR Home with Private Pool & BBQ — photo 2

Upstay Pristine 3BR Home with Private Pool & BBQ — photo 3

Upstay Pristine 3BR Home with Private Pool & BBQ — photo 4

Upstay Pristine 3BR Home with Private Pool & BBQ — photo 5

Upstay Pristine 3BR Home with Private Pool & BBQ

Clermont, Florida

3 bedrooms · 6 beds · 3 bathrooms

From$106/ night

Upstay: Crystal Cove Resort Villa w/ Pool & Games — photo 1

Upstay: Crystal Cove Resort Villa w/ Pool & Games — photo 2

Upstay: Crystal Cove Resort Villa w/ Pool & Games — photo 3

Upstay: Crystal Cove Resort Villa w/ Pool & Games — photo 4

Upstay: Crystal Cove Resort Villa w/ Pool & Games — photo 5

Upstay: Crystal Cove Resort Villa w/ Pool & Games

Kissimmee, Florida

4 bedrooms · 5 beds · 3 bathrooms

From$175/ night

The Gerrard | New Unit Near FIFA 2026 — photo 1

The Gerrard | New Unit Near FIFA 2026 — photo 2

The Gerrard | New Unit Near FIFA 2026 — photo 3

The Gerrard | New Unit Near FIFA 2026 — photo 4

The Gerrard | New Unit Near FIFA 2026 — photo 5

The Gerrard | New Unit Near FIFA 2026

Toronto, Canada

2 bedrooms · 2 beds · 2 bathrooms

FromCA$175/ night

Waterfront Family Mansion w BBQ, Games Room & Pool — photo 1

Waterfront Family Mansion w BBQ, Games Room & Pool — photo 2

Waterfront Family Mansion w BBQ, Games Room & Pool — photo 3

Waterfront Family Mansion w BBQ, Games Room & Pool — photo 4

Waterfront Family Mansion w BBQ, Games Room & Pool — photo 5

Waterfront Family Mansion w BBQ, Games Room & Pool

Kissimmee, Florida

8 bedrooms · 10 beds · 5 bathrooms

From$230/ night

Pet-friendly Condo Pool, Sauna—Near Disney — photo 1

Pet-friendly Condo Pool, Sauna—Near Disney — photo 2

Pet-friendly Condo Pool, Sauna—Near Disney — photo 3

Pet-friendly Condo Pool, Sauna—Near Disney — photo 4

Pet-friendly Condo Pool, Sauna—Near Disney — photo 5

Pet-friendly Condo Pool, Sauna—Near Disney

Winter Garden, Florida

3 bedrooms · 4 beds · 2 bathrooms

Upstay Spacious Home w Patio Vista Cay Resort — photo 1

Upstay Spacious Home w Patio Vista Cay Resort — photo 2

Upstay Spacious Home w Patio Vista Cay Resort — photo 3

Upstay Spacious Home w Patio Vista Cay Resort — photo 4

Upstay Spacious Home w Patio Vista Cay Resort — photo 5

Upstay Spacious Home w Patio Vista Cay Resort

Orlando, Florida

3 bedrooms · 8 beds · 2 bathrooms

From$130/ night

The Gerrard | Watch Party Ready Basement — photo 1

The Gerrard | Watch Party Ready Basement — photo 2

The Gerrard | Watch Party Ready Basement — photo 3

The Gerrard | Watch Party Ready Basement — photo 4

The Gerrard | Watch Party Ready Basement — photo 5

The Gerrard | Watch Party Ready Basement

Toronto, Canada

2 bedrooms · 2 beds · 1 bathroom

FromCA$183/ night

Elegant Suite w Patio, BBQ Grill! — photo 1

Elegant Suite w Patio, BBQ Grill! — photo 2

Elegant Suite w Patio, BBQ Grill! — photo 3

Elegant Suite w Patio, BBQ Grill! — photo 4

Elegant Suite w Patio, BBQ Grill! — photo 5

Elegant Suite w Patio, BBQ Grill!

Toronto, Canada

3 bedrooms · 4 beds · 2 bathrooms

FromCA$197/ night

Upstay Condo Near Disney w Pool & Sauna — photo 1

Upstay Condo Near Disney w Pool & Sauna — photo 2

Upstay Condo Near Disney w Pool & Sauna — photo 3

Upstay Condo Near Disney w Pool & Sauna — photo 4

Upstay Condo Near Disney w Pool & Sauna — photo 5

Upstay Condo Near Disney w Pool & Sauna

Winter Garden, Florida

3 bedrooms · 3 beds · 2 bathrooms

Spacious 4BR Family Townhouse—Private Pool & BBQ — photo 1

Spacious 4BR Family Townhouse—Private Pool & BBQ — photo 2

Spacious 4BR Family Townhouse—Private Pool & BBQ — photo 3

Spacious 4BR Family Townhouse—Private Pool & BBQ — photo 4

Spacious 4BR Family Townhouse—Private Pool & BBQ — photo 5

Spacious 4BR Family Townhouse—Private Pool & BBQ

Kissimmee, Florida

4 bedrooms · 5 beds · 3 bathrooms

From$160/ night

Modern 3BR Condo w Private Patio 7min to Disney — photo 1

Modern 3BR Condo w Private Patio 7min to Disney — photo 2

Modern 3BR Condo w Private Patio 7min to Disney — photo 3

Modern 3BR Condo w Private Patio 7min to Disney — photo 4

Modern 3BR Condo w Private Patio 7min to Disney — photo 5

Modern 3BR Condo w Private Patio 7min to Disney

Winter Garden, Florida

3 bedrooms · 4 beds · 2 bathrooms

Modern 3BR Resort Condo with Pool near Disney — photo 1

Modern 3BR Resort Condo with Pool near Disney — photo 2

Modern 3BR Resort Condo with Pool near Disney — photo 3

Modern 3BR Resort Condo with Pool near Disney — photo 4

Modern 3BR Resort Condo with Pool near Disney — photo 5

Modern 3BR Resort Condo with Pool near Disney

Winter Garden, Florida

3 bedrooms · 4 beds · 2 bathrooms

Upstay: Large Resort Home w Private Pool & Hot Tub — photo 1

Upstay: Large Resort Home w Private Pool & Hot Tub — photo 2

Upstay: Large Resort Home w Private Pool & Hot Tub — photo 3

Upstay: Large Resort Home w Private Pool & Hot Tub — photo 4

Upstay: Large Resort Home w Private Pool & Hot Tub — photo 5

Upstay: Large Resort Home w Private Pool & Hot Tub

Kissimmee, Florida

7 bedrooms · 10 beds · 6.5 bathrooms

From$170/ night