Holiday Rentals in Winter Park

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Winter Park

The View Studio Suites and Event Venue
3.0 star property
8.4 out of 10, Very good, (1308)
"We had a great stay! "
The price is €62
includes taxes & fees
19 Oct - 20 Oct
The View Studio Suites and Event Venue
Florida Hotel & Conference Center in the Florida Mall
3.5 star property
9.2 out of 10, Wonderful, (2164)
"The room was very clean and the front desk staff was very courteous."
Florida Hotel & Conference Center in the Florida Mall
Floridays Resort Orlando
3.5 star property
8.6 out of 10, Excellent, (11545)
"Great staff and clean rooms. Tatiana at the front desk is amazing. She took great care of us. "
The price is €181
includes taxes & fees
19 Oct - 20 Oct
Floridays Resort Orlando
Lake Buena Vista Resort Village & Spa
4.0 star property
8.4 out of 10, Very good, (9225)
"Amazing stay "
Lake Buena Vista Resort Village & Spa
The Point Hotel & Suites
3.5 star property
8.0 out of 10, Very good, (3282)
"Perfect location to nearby theme parks. The room was clean and staff were so helpful. Will definitely stay again!"
The price is €112
includes taxes & fees
4 Nov - 5 Nov
The Point Hotel & Suites
Blue Tree Resort at Lake Buena Vista
3.0 star property
8.6 out of 10, Excellent, (1802)
"The staff were a great help and friendly and the room was very clean and organized well. The resort was beautiful my kids and I loved it and will be visiting again."
Blue Tree Resort at Lake Buena Vista
The Point by Edge
4.0 star property
8.4 out of 10, Very good, (792)
"Gorgeous room and friendly staff."
The price is €66
includes taxes & fees
27 Oct - 28 Oct
The Point by Edge
Parc Corniche Condominium Suite Hotel
3.0 star property
8.0 out of 10, Very good, (2170)
"Is close to Seaworld and Aquatica, good option to stay in this hotel "
The price is €118
includes taxes & fees
16 Oct - 17 Oct
Parc Corniche Condominium Suite Hotel
Vista Cay Resort by Millenium at Universal Blvd
3.5 star property
8.6 out of 10, Excellent, (1559)
"Enjoy my stay always "
Vista Cay Resort by Millenium at Universal Blvd
Sonder by Marriott Bonvoy Vista Cay Apartments
3.5 star property
9.0 out of 10, Wonderful, (249)
"I love this property it was clean and the pool was fabulous. The concierge was helpful and friendly i definitely will be staying there again"
The price is €110
includes taxes & fees
26 Oct - 27 Oct
Sonder by Marriott Bonvoy Vista Cay Apartments
WorldQuest Orlando Resort
4.0 star property
8.4 out of 10, Very good, (4008)
"Always love staying here with my family and friends for over 10 years now great location for Disney parks and easy to get groceries and dining options. Close to Vinland shopping as well."
WorldQuest Orlando Resort
Century Millenia
3.0 star property
9.0 out of 10, Wonderful, (92)
"The property was clean and a good condition "
Century Millenia
Blue Heron Beach Resort
3.5 star property
8.4 out of 10, Very good, (2964)
"Very clean room and nice pool, is a perfect resort easy location of disney and sea word ,epcot, universal ,island of adventure very nice i like this resort"
Blue Heron Beach Resort
Wellborn Hotel Downtown, Sonder by Marriott Bonvoy
4.0 star property
8.2 out of 10, Very good, (315)
"The staff was great, the room was really nice and comfortable, the ambiance was great "
The price is €82
includes taxes & fees
10 Nov - 11 Nov
Wellborn Hotel Downtown, Sonder by Marriott Bonvoy
Enchanted Fantasy
3.5 star property
The price is €117
includes taxes & fees
15 Oct - 16 Oct
Enchanted Fantasy
staySky Suites - I Drive Orlando
3.0 star property
7.8 out of 10, Good, (1232)
"Excellent option for those visiting the park "
The price is €80
includes taxes & fees
15 Oct - 16 Oct
staySky Suites - I Drive Orlando
Orlando's Sunshine Resort
3.5 star property
9.2 out of 10, Wonderful, (233)
"great location "
Orlando's Sunshine Resort
Marriott's Sabal Palms
4.0 star property
9.6 out of 10, Exceptional, (202)
"Easy check in, pool was awesome "
The price is €222
includes taxes & fees
5 Nov - 6 Nov
Marriott's Sabal Palms
Premium Condos near Universal Studios
3.5 star property
9.2 out of 10, Wonderful, (21)
"The condo was amazing. Comfortable, clean and quiet with no issues. Property management was great. Communication was very good and helpful. I would give it a 10 plus. Would definitely come back "
The price is €135
includes taxes & fees
19 Oct - 20 Oct
Premium Condos near Universal Studios
Modern Luxury Villa with Everything
9.8 out of 10, Exceptional, (441)
"It was a great stay. The house was clean and close to everything."
Modern Luxury Villa with Everything
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Park Hotel Reviews

Find out more about Winter Park

Everything you need to know about Winter Park holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Park holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winter Park holiday 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  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter Park holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter Park holiday rentals we have selected for you start as low as €62 per night. Entering your travel 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 holiday 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 holiday.

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. 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 holiday rentals in Winter Park?

Yes, there are holiday rentals in Winter Park close to Kraft Azalea Gardens, or you can select 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 are some of the best holiday rentals that Winter Park has to offer?

Marriott's Sabal Palms: This holiday home rental outside of Winter Park is located near the airport, and has an outdoor pool, a balcony and a BBQ 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 outdoor tennis court and 1 hot tub.

How many holiday rentals are there in Winter Park?

Expedia has 64 holiday 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 Lake Virginia 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 holiday rentals like in Winter Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Park. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for families.