Hotels with a Pool in Winter Garden

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Aug 20 - Aug 21
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Aug 21 - Aug 22
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Top 5 Hotels with a Pool in Winter Garden at a glance

  1. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center — 3-star hotel in Bay Lake. Guest rating: 9.4/10 — Exceptional.
  2. Home2 Suites by Hilton Orlando at Flamingo Crossings — 3-star hotel in Bay Lake. Guest rating: 9.4/10 — Exceptional.
  3. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance — 3-star hotel in Bay Lake. Guest rating: 9.6/10 — Exceptional.
  4. Home2 Suites By Hilton Winter Garden — 3-star hotel in Winter Garden. Guest rating: 9.4/10 — Exceptional.
  5. TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance — 3.5-star hotel in Bay Lake. Guest rating: 9.0/10 — Wonderful.

Hotels with a Pool in Winter Garden

A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.
A Marriott Fairfield hotel sign with a landscaped garden in front.
A lobby with a central seating area, wooden ceiling, and patterned carpet.

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Pool loungers
$77
$87 total
includes taxes & fees
Aug 31 - Sep 1
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.
A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.
A restaurant with a bar area, seating, and a view of greenery outside.
A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Outdoor pool
  • Pool loungers
$93
$105 total
includes taxes & fees
Aug 30 - Aug 31
Home2 Suites by Hilton Orlando at Flamingo Crossings
A hotel pool area with lounge chairs, a fire pit, and a large pool.
A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.
A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.
A modern bathroom with a large mirror, two sinks, and a glass-enclosed shower area.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Pool loungers
$82
$93 total
includes taxes & fees
Sep 7 - Sep 8
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A swimming pool with lounge chairs and a view of a building in the background.
A hotel room with a kitchenette, a sofa, a desk, and a dining area.
An outdoor patio with round tables and chairs, a red umbrella, and a grill.
A hotel entrance with a sign reading "HOME 2 SUITES BY HILTON".

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
  • Outdoor pool
$107
$120 total
includes taxes & fees
Sep 6 - Sep 7
Home2 Suites By Hilton Winter Garden
A pool area with lounge chairs, a fire pit, and palm trees.
A restaurant with outdoor seating, a fire feature, and a bar area.
A lounge area with a fire feature, wicker furniture, and a bar in the background.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Hot tub
$93
$104 total
includes taxes & fees
Aug 30 - Aug 31
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A hotel room with a desk, chair, and bed.
A restaurant with outdoor seating, a bar, and a fire feature.

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Hot tub
$87
$98 total
includes taxes & fees
Aug 30 - Aug 31
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.
A hotel room with a large window, a pool view, a chair, a table, a lamp, and a bed.
An outdoor patio with a barbecue grill, dining area, and umbrella.
A large hotel with a central entrance, multiple floors, and a sign indicating 'Homewood Suites by Hilton.'

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Outdoor pool
  • Pool loungers
$106
$119 total
includes taxes & fees
Aug 30 - Aug 31
Homewood Suites by Hilton Orlando at Flamingo Crossings
A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.
A modern living room with a sofa, ottoman, and a TV on a stand.
A hotel with a blue roof, a reflection pool, and palm trees.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
  • 2 outdoor pools
  • Poolside bar
  • Pool loungers
  • Hot tub
$94
$134 total
includes taxes & fees
Sep 13 - Sep 14
Hilton Vacation Club Aqua Sol Orlando West
A resort with a large pool, water slides, palm trees, and beach umbrellas.
A resort with multiple swimming pools surrounded by lush greenery and a large hotel building.
A couple walking past a surfboard and a 'Longboard Bar and Grill' sign.
A modern lobby with a reception desk, seating area, and a bar.

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
  • 6 outdoor pools
  • 3 poolside bars
  • Pool loungers
  • 2 hot tubs
$169
$245 total
includes taxes & fees
Aug 23 - Aug 24
The Grove Resort & Water Park Orlando
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.
A modern kitchen with a dishwasher, a dining area with a table and chairs, and a view of the outside.
A spacious living area with a sofa, coffee table, and a view of the kitchen.

Upstay Disney Pet Friendly Condo w Pool Spa Games

Upstay Disney Pet Friendly Condo w Pool Spa Games
Winter Garden
  • Outdoor pool
$82
$237 total
includes taxes & fees
Sep 8 - Sep 9
Upstay Disney Pet Friendly Condo w Pool Spa Games
An aerial view of a resort with a large central pool, multiple lounge areas, and surrounding greenery.
A modern living room with a sofa, two small tables, a ceiling fan, a TV, and a balcony with outdoor furniture.

Upstay 3BR Condo w Pool Patio Near Disney

Upstay 3BR Condo w Pool Patio Near Disney
Winter Garden
  • Free parking
  • Free WiFi
$93
$281 total
includes taxes & fees
Aug 24 - Aug 25
Upstay 3BR Condo w Pool Patio Near Disney
A spacious living room with a sofa, a coffee table, and a TV. There is a balcony with a view of trees and buildings.

Upstay: 3BR Family Condo w Pool & Sauna

Upstay: 3BR Family Condo w Pool & Sauna
Winter Garden
  • Outdoor pool
$81
$259 total
includes taxes & fees
Aug 23 - Aug 24
Upstay: 3BR Family Condo w Pool & Sauna
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A dining area with a round table set for four, surrounded by wicker chairs.
A spacious living room with a grey sofa, a coffee table, and a large plant. There is a balcony with outdoor furniture and a TV mounted on the wall.

Upstay - Modern Family Apartment w Pool Hot Tub

Upstay - Modern Family Apartment w Pool Hot Tub
Winter Garden
  • Pet friendly
  • Free parking
  • Free WiFi
$105
$261 total
includes taxes & fees
Aug 24 - Aug 25
Upstay - Modern Family Apartment w Pool Hot Tub
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.

Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
  • Outdoor pool
$85
$263 total
includes taxes & fees
Sep 8 - Sep 9
Modern 3BR Resort Condo With Pool Near Disney
An aerial view of a resort with a large, irregularly shaped pool surrounded by lounge chairs and umbrellas, set against a backdrop of palm trees and a multi-story building.
A gym with exercise equipment, large windows, and a view of greenery.
A balcony with a view of a forest, a table with chairs, and a ceiling fan.
A modern kitchen with white cabinets, a stainless steel refrigerator, and a green accent wall.

Modern 3BR Condo Near Disney- Pool and Hot Tub

Modern 3BR Condo Near Disney- Pool and Hot Tub
Winter Garden
  • Pet friendly
  • Free parking
  • Free WiFi
$93
$250 total
includes taxes & fees
Sep 2 - Sep 3
Modern 3BR Condo Near Disney- Pool and Hot Tub
A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.

Upstay Condo Near Disney w Pool & Sauna

Upstay Condo Near Disney w Pool & Sauna
Winter Garden
  • Outdoor pool
$84
$262 total
includes taxes & fees
Sep 8 - Sep 9
Upstay Condo Near Disney w Pool & Sauna
A balcony with a view of a green landscape, a table with chairs, and a railing.

Upstay - Condo Near Disney w Pool Hot tub Sauna

Upstay - Condo Near Disney w Pool Hot tub Sauna
Winter Garden
  • Pet friendly
  • Free parking
  • Free WiFi
$88
$245 total
includes taxes & fees
Sep 9 - Sep 10
Upstay - Condo Near Disney w Pool Hot tub Sauna
A multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.
A spacious living room with a sofa, a coffee table, and a TV. There is a balcony with a view of trees and buildings.
A bedroom with a large bed, a bathroom with a bathtub, and a balcony with a view.

Condo With Sauna, Games, Poolnear Disney

Condo With Sauna, Games, Poolnear Disney
Winter Garden
  • Outdoor pool
$76
$253 total
includes taxes & fees
Sep 8 - Sep 9
Condo With Sauna, Games, Poolnear Disney
A pool area with lounge chairs and a small pool.
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A bathroom with two sinks, a large mirror, and a vanity with a light fixture.

Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
Winter Garden
  • Outdoor pool
$69
$245 total
includes taxes & fees
Sep 9 - Sep 10
Upstay: Condo Near Disney w Pool, Sauna
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A spacious living room with a large sliding glass door leading to a balcony, a ceiling fan, a flat-screen TV, and a minimalist furniture arrangement.
A covered balcony with two chairs, a ceiling fan, and a view of trees and a wooden deck.
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

Pet-friendly Resort Getaway With Patio and Pool

Pet-friendly Resort Getaway With Patio and Pool
Winter Garden
  • Outdoor pool
$87
$243 total
includes taxes & fees
Sep 8 - Sep 9
Pet-friendly Resort Getaway With Patio and Pool
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Discover your perfect hotel with a pool in Winter Garden

Breakfast included
Hot tub
4 stars
Water park
5 stars

Hotels with pools and free breakfast in Winter Garden

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.
A lobby with a central seating area, wooden ceiling, and patterned carpet.
A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.
A Marriott Fairfield hotel sign with a landscaped garden in front.

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Bay Lake
$77
$87 total
includes taxes & fees
Aug 31 - Sep 1
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
A large hotel with multiple floors, a central courtyard, and a reflective water feature.
A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.
A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.
A covered outdoor seating area with tables and chairs, a ceiling fan, and a view of a pool and buildings in the background.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
$82
$93 total
includes taxes & fees
Sep 7 - Sep 8
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.
A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.
A restaurant with a bar area, seating, and a view of greenery outside.
A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
$93
$105 total
includes taxes & fees
Aug 30 - Aug 31
Home2 Suites by Hilton Orlando at Flamingo Crossings
A pool area with lounge chairs, a fire pit, and palm trees.
A hotel room with a desk, chair, and bed.
A restaurant with outdoor seating, a bar, and a fire feature.

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
$87
$98 total
includes taxes & fees
Aug 30 - Aug 31
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
An outdoor patio with round tables and chairs, a red umbrella, and a grill.
A hotel room with a kitchenette, a sofa, a desk, and a dining area.
A swimming pool with lounge chairs and a view of a building in the background.
A hotel entrance with a sign reading "HOME 2 SUITES BY HILTON".

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
$107
$120 total
includes taxes & fees
Sep 6 - Sep 7
Home2 Suites By Hilton Winter Garden
A pool area with lounge chairs, a fire pit, and palm trees.
A restaurant with outdoor seating, a fire feature, and a bar area.
A lounge area with a fire feature, wicker furniture, and a bar in the background.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
$93
$104 total
includes taxes & fees
Aug 30 - Aug 31
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.
A hotel room with a large window, a pool view, a chair, a table, a lamp, and a bed.
An outdoor patio with a barbecue grill, dining area, and umbrella.
A large hotel with a central entrance, multiple floors, and a sign indicating 'Homewood Suites by Hilton.'

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
$106
$119 total
includes taxes & fees
Aug 30 - Aug 31
Homewood Suites by Hilton Orlando at Flamingo Crossings
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Hotels with pools and hot tubs in Winter Garden

A pool area with lounge chairs, a fire pit, and palm trees.
A hotel room with a desk, chair, and bed.
A restaurant with outdoor seating, a bar, and a fire feature.

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
$87
$98 total
includes taxes & fees
Aug 30 - Aug 31
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A restaurant with outdoor seating, a fire feature, and a bar area.
A lounge area with a fire feature, wicker furniture, and a bar in the background.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
$93
$104 total
includes taxes & fees
Aug 30 - Aug 31
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.
A modern living room with a sofa, ottoman, and a TV on a stand.
A modern living room with a teal accent wall, a sofa, ottomans, a dining area with white chairs, and a balcony with a view.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
$94
$134 total
includes taxes & fees
Sep 13 - Sep 14
Hilton Vacation Club Aqua Sol Orlando West
A resort with a large pool, water slides, palm trees, and beach umbrellas.
A resort with multiple swimming pools surrounded by lush greenery and a large hotel building.
A couple walking past a surfboard and a 'Longboard Bar and Grill' sign.
A modern lobby with a reception desk, seating area, and a bar.

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
$169
$245 total
includes taxes & fees
Aug 23 - Aug 24
The Grove Resort & Water Park Orlando
A modern living room with a sofa, two small tables, a ceiling fan, a TV, and a balcony with outdoor furniture.
An aerial view of a resort with a large central pool, multiple lounge areas, and surrounding greenery.

Upstay 3BR Condo w Pool Patio Near Disney

Upstay 3BR Condo w Pool Patio Near Disney
Winter Garden
$93
$281 total
includes taxes & fees
Aug 24 - Aug 25
Upstay 3BR Condo w Pool Patio Near Disney
A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.
A spacious living room with a grey sofa, a coffee table, and a large plant. There is a balcony with outdoor furniture and a TV mounted on the wall.
A dining area with a round table set for four, surrounded by wicker chairs.

Upstay - Modern Family Apartment w Pool Hot Tub

Upstay - Modern Family Apartment w Pool Hot Tub
Winter Garden
$105
$261 total
includes taxes & fees
Aug 24 - Aug 25
Upstay - Modern Family Apartment w Pool Hot Tub
A gym with exercise equipment, large windows, and a view of greenery.
A balcony with a view of a forest, a table with chairs, and a ceiling fan.
A modern kitchen with white cabinets, a stainless steel refrigerator, and a green accent wall.

Modern 3BR Condo Near Disney- Pool and Hot Tub

Modern 3BR Condo Near Disney- Pool and Hot Tub
Winter Garden
$93
$250 total
includes taxes & fees
Sep 2 - Sep 3
Modern 3BR Condo Near Disney- Pool and Hot Tub
A balcony with a view of a green landscape, a table with chairs, and a railing.
A modern living room with a TV, seating area, kitchen, and a ceiling fan.

Upstay - Condo Near Disney w Pool Hot tub Sauna

Upstay - Condo Near Disney w Pool Hot tub Sauna
Winter Garden
$88
$245 total
includes taxes & fees
Sep 9 - Sep 10
Upstay - Condo Near Disney w Pool Hot tub Sauna
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.
A modern kitchen with a dishwasher, a dining area with a table and chairs, and a view of the outside.
A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

Upstay - Condo Near Disney w Pool-spa-sauna-games

Upstay - Condo Near Disney w Pool-spa-sauna-games
Winter Garden
$82
$245 total
includes taxes & fees
Sep 8 - Sep 9
Upstay - Condo Near Disney w Pool-spa-sauna-games
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.
A view of a swimming pool surrounded by palm trees and lounge chairs, with a clear blue sky above.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A spacious lobby with a large sofa, a coffee table, and a TV mounted on the wall.

Upstay Modern 2BR Condo Near Disney

Upstay Modern 2BR Condo Near Disney
Winter Garden
$110
$276 total
includes taxes & fees
Aug 24 - Aug 25
Upstay Modern 2BR Condo Near Disney
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4-star hotels with pools in Winter Garden

A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.
A modern living room with a sofa, ottoman, and a TV on a stand.
A modern living room with a teal accent wall, a sofa, ottomans, a dining area with white chairs, and a balcony with a view.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
$94
$134 total
includes taxes & fees
Sep 13 - Sep 14
Hilton Vacation Club Aqua Sol Orlando West
A resort with a large pool, water slides, palm trees, and beach umbrellas.
A resort with multiple swimming pools surrounded by lush greenery and a large hotel building.
A couple walking past a surfboard and a 'Longboard Bar and Grill' sign.
A modern lobby with a reception desk, seating area, and a bar.

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
$169
$245 total
includes taxes & fees
Aug 23 - Aug 24
The Grove Resort & Water Park Orlando
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
Winter Garden
$69
$245 total
includes taxes & fees
Sep 9 - Sep 10
Upstay: Condo Near Disney w Pool, Sauna
A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.

Upstay Family-friendly Condo w Pool Near Disney

Upstay Family-friendly Condo w Pool Near Disney
Winter Garden
$81
$259 total
includes taxes & fees
Aug 24 - Aug 25
Upstay Family-friendly Condo w Pool Near Disney
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.

Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
$85
$263 total
includes taxes & fees
Sep 8 - Sep 9
Modern 3BR Resort Condo With Pool Near Disney
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.
A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.
A modern kitchen with a dishwasher, a dining area with a table and chairs, and a view of the outside.
A spacious living area with a sofa, coffee table, and a view of the kitchen.

Upstay Disney Pet Friendly Condo w Pool Spa Games

Upstay Disney Pet Friendly Condo w Pool Spa Games
Winter Garden
$82
$237 total
includes taxes & fees
Sep 8 - Sep 9
Upstay Disney Pet Friendly Condo w Pool Spa Games
A spacious living room with a large sliding glass door leading to a balcony, a ceiling fan, a flat-screen TV, and a minimalist furniture arrangement.
A modern living room with a sofa, coffee table, and a dining area with a TV.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

Pet-friendly Resort Getaway With Patio and Pool

Pet-friendly Resort Getaway With Patio and Pool
Winter Garden
$87
$243 total
includes taxes & fees
Sep 8 - Sep 9
Pet-friendly Resort Getaway With Patio and Pool
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.
A bathroom with a bathtub, a circular wall decoration, and a ceiling fan.

Upstay: Condo w Pool, Sauna for 6 Guests

Upstay: Condo w Pool, Sauna for 6 Guests
Winter Garden
$101
$259 total
includes taxes & fees
Aug 23 - Aug 24
Upstay: Condo w Pool, Sauna for 6 Guests
A view from a balcony overlooking a swimming pool with lounge chairs and palm trees.
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A spacious living area with a sofa, coffee table, and a view to the outside.

Spacious Resort Suite With Private Patio & Sauna

Spacious Resort Suite With Private Patio & Sauna
Winter Garden
$89
$245 total
includes taxes & fees
Sep 2 - Sep 3
Spacious Resort Suite With Private Patio & Sauna
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A balcony with a view of a construction site, a table with a vase of flowers, and two chairs.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

Bright Family Escape With Game Room and Sauna

Bright Family Escape With Game Room and Sauna
Winter Garden
$89
$245 total
includes taxes & fees
Sep 2 - Sep 3
Bright Family Escape With Game Room and Sauna
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top neighborhoods in Winter Garden

A street lined with large trees and historic brick buildings, including a 'Local' sign.
Photo by Shannon Maya
A tree-lined sidewalk with parked cars and a clear sky.
A bakery interior with a display case, shelves with jars, and a counter with a menu board.
Photo by JoyFilledWander
A café with a variety of food items and beverages on display, including boxes of snacks and bottles of wine.
Photo by JoyFilledWander
A bar with a polished floor, metal chairs, and a brick wall with a TV.
Photo by Nancy

Downtown Winter Garden

Plant Street bursts with small-town charm in Downtown Winter Garden. The restored 1935 Garden Theatre anchors the brick-lined pedestrian zone where locals and visitors stroll past historic storefronts. Hop on the West Orange Trail for a scenic bike ride or browse the weekly farmers market for fresh Florida citrus and artisanal goods. Farm-to-table restaurants with outdoor seating line the main drag, while boutique bed & breakfasts offer cozy accommodations in restored buildings. The pedestrian-friendly layout means you can park once and explore everything on foot, from antique shops to the Central Florida Railroad Museum.

Orlando, Florida Skyline

Horizon West

Winter Garden's Horizon West neighborhood has a host of places to visit such as Walt Disney World® Resort and Orange County National Golf Club.

A sunset over a body of water with silhouetted land in the distance and tall grasses in the foreground.

Vista del Lago

Vista del Lago is a peaceful retreat just minutes from Orlando's major attractions. Vacation homes with private pools and resort amenities offer the perfect landing spot after action-packed theme park days. Disney's Animal Kingdom and Magic Kingdom are just a short drive away, while community pools provide refreshing breaks between adventures. Dining options require a quick drive to nearby Championsgate or Disney Springs, where choices range from casual to upscale. Most travelers appreciate having rental cars to navigate between the quiet neighborhood and Orlando's entertainment districts. Many vacation rentals feature full kitchens and game rooms, creating the ideal home base for family theme park trips.

A wooden pier extending into a calm body of water, surrounded by lush greenery and a distant forest.
A calm lake with lily pads and reeds in the foreground, surrounded by trees and a cloudy sky.
Photo by Gregg Yutko

Oakland

Oakland's historic charm lives on through preserved Victorian homes and oak-canopied streets. Wander downtown to discover the 1889 Healthy House Museum and local artisan shops. The 128-acre Oakland Nature Preserve invites you to explore cypress wetlands and spot some of the 200+ bird species that call Lake Apopka home. Southern comfort food dominates the dining scene with most spots closing early. The area is best explored by car, though downtown remains pleasantly walkable. Cozy bed and breakfasts in historic homes offer an intimate alternative to Orlando's bustling tourist accommodations just 15 minutes away.

A wooden pier extending into a calm body of water, surrounded by lush greenery and a distant forest.

Killarney

Killarney offers a peaceful retreat from Orlando's tourist bustle while keeping adventure within reach. The Oakland Nature Preserve invites you to explore scenic trails while the nearby West Orange Trail is perfect for morning bike rides. Lake Apopka provides a serene backdrop for fishing or simply watching the sunset paint the Florida sky. When you're ready for more action, Winter Garden's charming downtown is just minutes away. Accommodation options include budget-friendly extended-stay hotels and vacation homes with pools and kitchenettes. A car is essential for getting around, though rideshare services are readily available. The quiet suburban streets make evening strolls pleasant after busy days exploring nearby attractions.

Top landmarks in Winter Garden

Flamingo Crossings Town Center

8.6/10 (131 reviews)
If you want to give your credit card some exercise, head out to Flamingo Crossings Town Center in Bay Lake.
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Disney's Palm Golf Course

8.4/10 (457 reviews)
You might want to practice your swing at Disney's Palm Golf Course, a golf course located 11.2 mi (18.1 km) from central Winter Garden. If Disney's Palm Golf Course doesn't quite scratch your golfing itch, Orange Lake Golf, and Disney's Lake Buena Vista Golf Course are also nearby.
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Disney's Magnolia Golf Course

8.4/10 (552 reviews)
You might want to play some rounds at Disney's Magnolia Golf Course, located 11.1 mi (17.9 km) from central Winter Garden. If Disney's Magnolia Golf Course doesn't quite scratch your golfing itch, Disney's Palm Golf Course, and Orange Lake Golf are also nearby.
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Orange County National Golf Club

8.4/10 (647 reviews)
You might want to play some rounds at Orange County National Golf Club, located 8.9 mi (14.4 km) from central Winter Garden. If Orange County National Golf Club doesn't quite scratch your golfing itch, Disney's Palm Golf Course, and Disney's Magnolia Golf Course are also nearby.
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Surfari Water Park

9.0/10 (2,086 reviews)
If thrills are what you're after, head to Surfari Water Park, located 2.3 mi (3.8 km) from central Four Corners. If you have fun at Surfari Water Park, you'll love Disney's Animal Kingdom® Theme Park and Island H2O Live!, both located nearby.
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West Orange Trail

8.4/10 (337 reviews)
Downtown Winter Garden is home to West Orange Trail, so why not stop by during your stay in Winter Garden. Winter Garden has other activities you might want to enjoy such as Kia Center.
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Disney's Oak Trail Golf Course

8.4/10 (377 reviews)
You might want to play some rounds at Disney's Oak Trail Golf Course, located 11.2 mi (18 km) from central Winter Garden. If Disney's Oak Trail Golf Course doesn't quite scratch your golfing itch, Disney's Palm Golf Course, and Orange Lake Golf are also nearby.
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Garden Theatre

8.4/10 (219 reviews)
If you want to see a show while you're in town, try and grab some tickets at Garden Theatre in Downtown Winter Garden. If you want to experience more of the culture Winter Garden has to offer, head to Winter Garden Art Association, West Orange Trail, and AdventHealth Winter Garden.
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