Hotels with a Pool in Winter Garden

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This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Hotels with a Pool in Winter Garden

Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, pool loungers

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.4 out of 10, Exceptional, (5,387 reviews)
Families dive into poolside bliss with dedicated shallow areas for little ones while adults sip refreshing cocktails from the swim-up bar. Sports enthusiasts appreciate nearby basketball courts and a well-equipped 24-hour fitness centre after Disney park explorations.
The price is £59
includes taxes & fees
30 Aug - 31 Aug
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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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Discover your perfect hotel with a pool in Winter Garden

Breakfast included
4 stars

Hotels with pools and free breakfast in Winter Garden

Free daily buffet breakfast
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (5387)
The price is £59
includes taxes & fees
30 Aug - 31 Aug
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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4-star hotels with pools in Winter Garden

Apartment (3 Bedrooms) | Front of property
Upstay 3BR Condo w Pool & Patio Near Disney

Upstay 3BR Condo w Pool & Patio Near Disney

Upstay 3BR Condo w Pool & Patio Near Disney
4.0 star property
Winter Garden
The price is £177
includes taxes & fees
17 Aug - 18 Aug
Upstay 3BR Condo w Pool & Patio Near Disney
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Hotels with pools and hot tubs in Winter Garden

Outdoor pool, a heated pool
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (2258)
The price is £65
includes taxes & fees
30 Aug - 31 Aug
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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 neighbourhoods in Winter Garden

A street lined with large trees and historic brick buildings, including a 'Local' sign.
Photo by Shannon Maya
Open Photo by Shannon Maya

Downtown Winter Garden

Plant Street bursts with small-town charm in City centre Winter Garden. The restored 1935 Garden Theatre anchors the brick-lined pedestrian zone where locals and visitors stroll past historic shopfronts. 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 cosy accommodation in restored buildings. The pedestrian-friendly layout means you can park once and explore everything on foot, from antique shops to the Central Florida Railway Museum.

Orlando, Florida Skyline

Horizon West

Winter Garden's Horizon West neighbourhood has lots 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. Holiday 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 travellers appreciate having rental cars to navigate between the quiet area and Orlando's entertainment districts. Many holiday 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.

Oakland

Oakland's historic charm lives on through preserved Victorian homes and oak-canopied streets. Wander city centre 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 city centre remains pleasantly walkable. Cosy bed and breakfasts in historic homes offer an intimate alternative to Orlando's bustling tourist accommodation 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 city centre is just minutes away. Accommodation options include budget-friendly extended-stay hotels and holiday 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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Frequently asked questions

What are the best hotels with a pool in Winter Garden?
With designer toiletries, pool sun loungers and the perfect setting for lounging by the water, Fairfield Inn & Suites Orlando Ocoee is a traveller favourite. Holiday Inn Express Hotel & Suites Ocoee East, an IHG Hotel is another popular Winter Garden hotel with a pool.
What are the cheapest hotels with a pool in Winter Garden?
It's a breeze to find some of the cheapest hotels in Winter Garden with a pool from £65 for your next getaway. One of the most affordable is Fairfield Inn & Suites Orlando Ocoee. It offers a terrace and pool sun loungers too. Holiday Inn Express Hotel & Suites Ocoee East, an IHG Hotel is another option where you can enjoy poolside fun without the premium price tag.
What is the best time to stay in a hotel with a pool in Winter Garden?
If you want the warmest weather, plan your trip for July. The temperatures are around 25ºC to 33ºC then. January has the coolest temperatures between 12ºC and 20ºC. For a more relaxed vibe and potentially cheaper Winter Garden hotels with a pool, visit in September when it's quieter.
What hotels with a pool are closest to Orange County National Golf Club?
Explore the sights and then lounge by the water at SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Centre/Western Entrance. Offering a cafe and a barbecue grill, this property is a quick drive from Orange County National Golf Club. Disney's Contemporary Resort is another option nearby. Check out the variety of hotels in Winter Garden with a pool that'll put you near this must-see attraction.
What hotels with a pool are closest to Orlando Intl. Airport (MCO)?
Recharge after a long flight with a swim at Hyatt Regency Orlando International Airport. It's around 2 km (1 mile) east of Orlando Intl. Airport (MCO). You can make the most of pillow top mattresses and hypo-allergenic bedding here too. Another nearby option is Homewood Suites by Hilton Orlando Airport. Book a room at one of these properties, or browse for other Winter Garden hotels with a pool close to the airport.
Are there any hotels with a pool in Winter Garden with parking?
There are 54,315 Winter Garden hotels with a pool and parking. Book a room at Fairfield Inn & Suites Orlando Ocoee, which has designer toiletries and pool sun loungers. Holiday Inn Express Hotel & Suites Ocoee East by IHG also combines the perks of a pool with the practicality of parking.

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