Vacation rentals in Winter Park

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Top vacation rentals in Winter Park

Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

4 out of 5
8113 Resort Village Drive, Orlando, FL
19.34 mi from city center
The price is $191 per night
$191
includes taxes & fees
$169 per night
May 1 - May 2
A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this condo resort. Enjoy the 3 hot tubs and perks like free self parking and a free theme park shuttle. 2 coffee shops/cafes, 2 bars/lounges, and a poolside bar offer an array of options for drinks and a bit to eat.
Pool
Hot Tub
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
1500 Sand Lake Road, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
11.23 mi from city center
The price is $209 per night
$209
includes taxes & fees
$186 per night
May 25 - May 26
This traditional aparthotel includes 3 restaurants, an outdoor pool, and a gym. Bring the family and enjoy the free theme park shuttle and kid-friendly dining. Enjoy the hot tub and perks like free WiFi.
Pool
Hot Tub
The View Studio Suites and Event Venue

The View Studio Suites and Event Venue

3 out of 5
9309 S Orange Blossom Trail, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
12.57 mi from city center
The price is $77 per night
$77
includes taxes & fees
$69 per night
May 1 - May 2
This aparthotel doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
Pet friendly
Floridays Resort Orlando

Floridays Resort Orlando

3.5 out of 5
12562 International Drive, Orlando, FL
17 mi from city center
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This smoke-free condo resort features 2 outdoor pools, a gym, and a restaurant. Families will appreciate the arcade/game room and onsite laundry facilities. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Kitchen
Blue Tree Resort at Lake Buena Vista

Blue Tree Resort at Lake Buena Vista

3 out of 5
12007 Cypress Run Road, Orlando, FL
17.64 mi from city center
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4 outdoor pools, 2 hot tubs, and an outdoor tennis court are all featured at this smoke-free aparthotel. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free WiFi and a free theme park shuttle.
Pool
Hot Tub
Sonder Vista Cay

Sonder Vista Cay

3.5 out of 5
4000 Breakview Drive, Orlando, FL
13.67 mi from city center
The price is $146 per night
$146
includes taxes & fees
$130 per night
May 28 - May 29
This aparthotel features an outdoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, concierge services, and barbecue grills are also on offer.
Pool
Kitchen
The Point Hotel & Suites

The Point Hotel & Suites

3.5 out of 5
7389 Universal Blvd, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
12.42 mi from city center
The price is $146 per night
$146
includes taxes & fees
$131 per night
May 7 - May 8
This aparthotel features an outdoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
Pool
Hot Tub
Sonder Wellborn

Sonder Wellborn

4 out of 5
211 N Lucerne Cir, Orlando, FL
4.97 mi from city center
The price is $101 per night
$101
includes taxes & fees
$90 per night
May 27 - May 28
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and a virtual front desk are also provided.
Parking included
Free WiFi
Parc Corniche Condominium Suite Hotel

Parc Corniche Condominium Suite Hotel

3 out of 5
6300 Parc Corniche Drive, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
15.78 mi from city center
The price is $134 per night
$134
includes taxes & fees
$119 per night
May 1 - May 2
This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. There's fun for all ages with a children's pool and a theme park shuttle, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
Sonder at The Point

Sonder at The Point

4 out of 5
7389 Universal Boulevard, Orlando, FL
12.42 mi from city center
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This aparthotel features an outdoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Free self parking, concierge services, and a virtual front desk are also on offer.
Pool
Parking included
Orlando Lakefront Tiny House Community

Orlando Lakefront Tiny House Community

3 out of 5
3405 N Orange Blossom Trail, Orlando, FL
4.3 mi from city center
The price is $157 per night
$157
includes taxes & fees
$139 per night
May 5 - May 6
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.
Kitchen
Pet friendly
WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
8849 Worldquest Blvd, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
20.04 mi from city center
The price is $290 per night
$290
includes taxes & fees
$258 per night
May 6 - May 7
This aparthotel features an outdoor pool and a 24-hour gym. Families will appreciate the free theme park shuttle and onsite laundry facilities. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi.
Pool
Kitchen
Blue Heron Beach Resort

Blue Heron Beach Resort

3.5 out of 5
13428 Blue Heron Beach Drive, Orlando, FL
18.77 mi from city center
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2 outdoor pools, a hot tub, and a gym are all featured at this aparthotel. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi.
Pool
Hot Tub
staySky Suites - I Drive Orlando

staySky Suites - I Drive Orlando

3 out of 5
12.88 mi from city center
The price is $96 per night
$96
includes taxes & fees
$85 per night
May 6 - May 7
This aparthotel features an outdoor pool and a 24-hour gym. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the hot tub and perks like free self parking and free WiFi.
Pool
Hot Tub
Modern Luxury Villa with Everything

Modern Luxury Villa with Everything

19.78 mi from city center
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A water park and a gym are featured at this smoke-free villa. Families will appreciate the arcade/game room and onsite laundry facilities.
Pool
Kitchen
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See all available properties in Winter Park
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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.

The next time you’re looking to get away from it all, head to Winter Park in central Florida. You’ll feel less like a tourist visiting for the first time and more like a local taking a casual stroll when you reserve one of many luxurious Winter Park vacation rentals. Stay within walking distance of the city’s 11-acre Central Park, or use your private accommodation as a resting place between trips to nearby Walt Disney World® and Universal Orlando.

The Local Life

Home to a charming downtown district with brick-lined streets, Winter Park is the perfect vacation destination for those who want to slow down and enjoy life for a while. Instead of driving all over town, stay in the heart of all the action by booking a convenient apartment rental in the center of the city. Once in your chosen accommodation, you can wake up at your leisure and wander into an inviting café for a light breakfast of croissants and cappuccinos. Snap a few photos of the stunning oak trees around the city, and take in the massive amount of vegetation inside the city’s Mead Botanical Garden. After exploring the Charles Hosmer Morse Museum of American Art, retreat to your quiet accommodation for an evening of sipping local wine on your personal patio.

For travelers looking to perfect their swing on the green during their trip to Florida, there’s no better place to stay than Extended Stay America, as its location is close to several golf courses. Traveling with the family in tow? Stay at the DoubleTree by Hilton Orlando Airport and enjoy the area’s many theme parks and attractions while staying reasonably close to Orlando International Airport. Travelocity offers accommodations throughout Florida—including Winter Park and Orlando—that will open up a world of possibility for your travels. Peruse the array of options we have available today, and start planning your picture-perfect trip to Winter Park.