Winter Park Vacation Rentals

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Vacation Rentals in Winter Park

DoubleTree by Hilton at the Entrance to Universal Orlando
4 out of 5
5780 Major Blvd, Orlando, FL, 32819
Fully refundableReserve now, pay when you stay
The price is $92 per night from Dec 13 to Dec 14
$92
per night
Dec 13 - Dec 14
Stay at this 4-star family-friendly aparthotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
4.2/5 Very Good! (6,359 reviews)
Universal Stay and Play
"The hotel was close enough to Universal to be convenient but not so close that it was out of my budget. Clean, modern, and has plenty of amenities, including a Starbucks."

Reviewed on Dec 6, 2022

DoubleTree by Hilton at the Entrance to Universal Orlando
Universal's Cabana Bay Beach Resort
3.5 out of 5
6550 Adventure Way, Orlando, FL, 32819
Fully refundableReserve now, pay when you stay
The price is $146 per night from Dec 22 to Dec 23
$146
per night
Dec 22 - Dec 23
Stay at this 3.5-star family-friendly aparthotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the ...
4.3/5 Excellent! (4,840 reviews)
Affordable
"Kalab was awesome at check-in. The property is one of our favorites on property of Universal for the price, and the kid friendliness. Lazy river, two pools, bowling alley, affordable."

Reviewed on Dec 6, 2022

Universal's Cabana Bay Beach Resort
Caribe Royale Orlando
4.5 out of 5
8101 World Center Dr, Orlando, FL, 32821
Fully refundable
The price is $172 per night from Dec 13 to Dec 14
$172
per night
Dec 13 - Dec 14
Stay at this 4.5-star luxury aparthotel in Orlando. Enjoy 3 outdoor pools, 3 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
4.3/5 Excellent! (3,717 reviews)
Love it!
"Fist time staying here. Everything was beautiful. Felt very safe. Room were very spacious. We will definitely stay here again. Also, location is everything. We were so close to Disney Springs & near by restaurant. LOVE IT!"

Reviewed on Dec 5, 2022

Caribe Royale Orlando

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Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
3.5 out of 5
14500 Continental Gateway, Orlando, FL, 32821
Fully refundable
The price is $79 per night from Dec 8 to Dec 9
$79
per night
Dec 8 - Dec 9
Stay at this 3.5-star family-friendly aparthotel in Orlando. Enjoy 2 outdoor pools, 3 spa tubs, and a water park. Our guests praise the pool and the helpful ...
3.4/5 (3,388 reviews)
"The waterpark was great for the kids."

Reviewed on Dec 6, 2022

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Grande Villas Resort
3.5 out of 5
12118 Turtle Cay Circle, Orlando, FL, 32836
Fully refundableReserve now, pay when you stay
The price is $132 per night from Dec 7 to Dec 8
$132
per night
Dec 7 - Dec 8
Stay at this 3.5-star family-friendly aparthotel in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the ...
4.5/5 Wonderful! (2,787 reviews)
"We had a great time here. The resort is charming, and the staff is friendly and helpful. The living room furniture and carpets could use a refresh. The beds are very comfortable, and the room is clean. We stayed in a room that faced the pool, and sometimes it got a little loud, so if you want quiet, ..."

Reviewed on Dec 6, 2022

Grande Villas Resort
Avanti International Resort
3 out of 5
8738 International Dr, Orlando, FL, 32819
Fully refundableReserve now, pay when you stay
The price is $95 per night from Dec 7 to Dec 8
$95
per night
Dec 7 - Dec 8
Stay at this 3-star family-friendly aparthotel in Orlando. Enjoy free WiFi, breakfast, and a free theme park shuttle. Our guests praise the bar and the helpful ...
3.3/5 (4,321 reviews)
"Very nice stay. Staff were nice and friendly, I e joyed the one night love the easy check out."

Reviewed on Dec 6, 2022

Avanti International Resort
Hyatt Regency Orlando
4.5 out of 5
9801 International Dr, Orlando, FL, 32819
Fully refundable
The price is $149 per night from Dec 18 to Dec 19
$149
per night
Dec 18 - Dec 19
Stay at this 4.5-star luxury aparthotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
4.5/5 Wonderful! (2,222 reviews)
"Loved this hotel! the pool area was amazing, although the bar near the pool was being renovated! loved the texting feature for front desk service; only thing that sucked was so much per night for parking garage, seems pretty ridiculous when the hotel stay is already a big chunk (parking should be ..."

Reviewed on Nov 30, 2022

Hyatt Regency Orlando
Cypress Pointe Resort by Diamond Resorts
3 out of 5
8651 Treasure Cay Lane, Orlando, FL, 32836
Fully refundableReserve now, pay when you stay
The price is $85 per night from Dec 7 to Dec 8
$85
per night
Dec 7 - Dec 8
Stay at this 3-star family-friendly aparthotel in Orlando. Enjoy free WiFi, free parking, and a children's pool. Our guests praise the pool and the helpful staff ...
4.3/5 Excellent! (2,134 reviews)
"This resort was very clean and had everything you could want or need. Only thing I can say thats negative is they need elevators and more parking. Have great food menu for store on site from Breakfast-Dinner. No need to have to leave! Pools, tennis, basketball, mini-golf, grills (can borrow Utensils ..."

Reviewed on Dec 4, 2022

Cypress Pointe Resort by Diamond Resorts
Best Western Orlando Gateway Hotel
2.5 out of 5
7299 Universal Blvd, Orlando, FL, 32819
Fully refundableReserve now, pay when you stay
The price is $63 per night from Dec 7 to Dec 8
$63
per night
Dec 7 - Dec 8
Stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, free parking, and 2 spa tubs. Our guests praise the pool and the helpful staff in our reviews. ...
4/5 Very Good! (2,707 reviews)
"Aunque la primera habitación que nos asignaron no estuvo muy acorde a nuestras expectativas nos cambiaron a una que estuvo mejor, Mariana fue muy profesional."

Reviewed on Dec 4, 2022

Best Western Orlando Gateway Hotel
Floridays Resort Orlando
3.5 out of 5
12562 International Drive, Orlando, FL, 32821
The price is $144 per night from Dec 7 to Dec 8
$144
per night
Dec 7 - Dec 8
Stay at this 3.5-star family-friendly condo in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
4.3/5 Excellent! (11,145 reviews)
"Very clean nice location spacious"

Reviewed on Dec 5, 2022

Floridays Resort Orlando
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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.

Other types of properties in Winter Park you may be interested in

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL, 32819
Fully refundableReserve now, pay when you stay
DoubleTree by Hilton at the Entrance to Universal Orlando
Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

3 out of 5
7125 Universal Boulevard, Orlando, FL, 32819
Fully refundableReserve now, pay when you stay
Universal's Endless Summer Resort - Dockside Inn and Suites
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.

Everything you need to know about Winter Park vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Park vacation rental for you. At Expedia, you can take your pick from vacation rentals, private vacation homes, apartments, condos, resorts, cabins, villas, hotels. The list goes on, and on... and on.. 

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Park vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. Explore our selection of Florida accommodations

Winter Park vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Park. If you’re looking for a little peace, consider booking during the quieter months, such as October or November. For more hustle and bustle, you may prefer to visit in July or August. 

Prices vary throughout the year. Winter is the cheapest time to visit, with Summer the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, the selection of Winter Park vacation rentals we have selected for you on this page range between $63 per night and $172 per night. Entering your desired dates in the search wizard you might find even better deals

How to find incredible deals on Winter Park rentals

At Expedia, we put the best Winter Park vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winter Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Park vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Park. Or explore even further and have a look at our vacation rentals in Key West, Panama City rentals or Destin accommodation rentals. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find vacation rentals in Winter Park?

Yes, we offer vacation rentals in Winter Park close to Kraft Azalea Gardens, or you can choose a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Winter Park. Make sure you have time to check out the university setting and gardens during your trip.

What's the top vacation rental that Winter Park has to offer?

Marriott's Sabal Palms: Visitors like this Winter Park vacation home rental. It is located next to a golf course and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with an arcade game room and a hot tub.

How many vacation rentals are there in Winter Park?

Expedia has 55 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens, whereas Kraft Azalea Gardens and Howell Branch Preserve Pavilion are a couple of picturesque spots to enjoy the outdoors. Universal Studios Florida and Universal Orlando Resort are other popular places to visit in the area.

What are vacation rentals like in Winter Park?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Winter Park. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.

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