Winter Park Vacation Rentals

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Vacation Rentals in Winter Park

Hyatt Regency Orlando International Airport
Meeting facility
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, 5,156 reviews
"Nice place to stay prior to cruise transportation "
The price is $224
includes taxes & fees
$199 per night
Jul 30 - Jul 31
Hyatt Regency Orlando International Airport
Avanti International Resort
Outdoor pool, pool umbrellas, sun loungers
Avanti International Resort
3.0 star property
7.8 out of 10, Good, 2,438 reviews
"We enjoyed our stay and utilzed the fitness room and pool the most! We walked to dinner and felt safe in the area!!!"
The price is $95
includes taxes & fees
$84 per night
Aug 5 - Aug 6
Avanti International Resort
Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas
Lake Buena Vista Resort Village & Spa
4.0 star property
8.4 out of 10, Very Good, 7,662 reviews
"Nice place to stay with family "
The price is $214
includes taxes & fees
$190 per night
Jul 28 - Jul 29
Lake Buena Vista Resort Village & Spa
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Terrace/patio
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
3.0 star property
7.0 out of 10, Good, 2,617 reviews
"Stuff are soooo kind the reception just the breakfast isn’t the greatest in having too much options to choose from . The only thing I would say is they have to hire more reception and schedule them during check out and check in time frame .. it’s hard to get a maid to clean your room upon request but over all view and hotel it’s amazing "
The price is $130
includes taxes & fees
$116 per night
Jul 28 - Jul 29
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Floridays Resort Orlando
2 outdoor pools, a heated pool, pool umbrellas, sun loungers
Floridays Resort Orlando
3.5 star property
8.6 out of 10, Excellent, 10,858 reviews
"I celebrated my 50th birthday here with 6 friends. We were in the 3 bedroom suite and we had plenty of room. The beds were comfortable and each room had its own TV which was great. The customer service was beyond amazing! Anytime I called, the request was fulfilled quickly. I recommend Floriday's and I would definitely stay again."
The price is $210
includes taxes & fees
$186 per night
Aug 5 - Aug 6
Floridays Resort Orlando
The View Studio Suites and Event Venue
Property entrance
The View Studio Suites and Event Venue
3.5 star property
8.4 out of 10, Very Good, 293 reviews
"one of the best I've stayed at in terms of value for money, I'll definitely be back and have already recommended it to friends"
The price is $90
includes taxes & fees
$80 per night
Jul 28 - Jul 29
The View Studio Suites and Event Venue
Holiday Inn & Suites Across From Universal Orlando, an IHG Hotel
Terrace/patio
Holiday Inn & Suites Across From Universal Orlando, an IHG Hotel
3.0 star property
7.2 out of 10, Good, 690 reviews
"There wasnt anything i didnt like it was awesome and the staff was wonderful i will stay again if im ever back intown"
The price is $102
includes taxes & fees
$87 per night
Aug 1 - Aug 2
Holiday Inn & Suites Across From Universal Orlando, an IHG Hotel
Embassy Suites by Hilton Orlando International Dr ICON Park
Lobby
Embassy Suites by Hilton Orlando International Dr ICON Park
3.5 star property
8.6 out of 10, Excellent, 1,649 reviews
"Loved our stay will definitely book again for our next stay"
The price is $110
includes taxes & fees
$98 per night
Aug 11 - Aug 12
Embassy Suites by Hilton Orlando International Dr ICON Park
Wingate by Wyndham - Orlando International Airport
Pillowtop beds, in-room safe, desk, blackout drapes
Wingate by Wyndham - Orlando International Airport
3.0 star property
8.8 out of 10, Excellent, 4,249 reviews
"Front desk staff was extremely accommodating & helpful. Thank you!"
The price is $99
includes taxes & fees
$88 per night
Jul 28 - Jul 29
Wingate by Wyndham - Orlando International Airport
The Point Hotel & Suites
Outdoor pool
The Point Hotel & Suites
3.5 star property
8.0 out of 10, Very Good, 3,017 reviews
"The property was nice but need more entry ways to get in the building. "
The price is $107
includes taxes & fees
$97 per night
Aug 4 - Aug 5
The Point Hotel & Suites
Orlando Lakefront Tiny House Community
The Club House | Individually decorated, individually furnished, laptop workspace
Orlando Lakefront Tiny House Community
3.0 star property
9.4 out of 10, Exceptional, 183 reviews
"Literally the most understanding host we’ve ever encountered! Was always willing to work with us and made this a very comfortable stay for me and my siblings. We will definitely be back."
The price is $155
includes taxes & fees
$137 per night
Jul 28 - Jul 29
Orlando Lakefront Tiny House Community
Embassy Suites by Hilton Orlando Lake Buena Vista South
2 restaurants, lunch, dinner served; American cuisine
Embassy Suites by Hilton Orlando Lake Buena Vista South
3.5 star property
9.2 out of 10, Wonderful, 1,791 reviews
"I really like staying at Embassy hotels, this one was my second stay in Florida and it was ok, but they can use new furniture in the lobby room sofas looked aged. In the shower there was a smell of mildew that can use attention to, the omelette for breakfast were so so not like the ones they make in San Juan Pr embassy, also I felt bug while sleeping that freaked me out the one night. Overall it was ok. "
The price is $159
includes taxes & fees
$140 per night
Aug 4 - Aug 5
Embassy Suites by Hilton Orlando Lake Buena Vista South
Sonder at The Point
Outdoor pool, pool umbrellas, sun loungers
Sonder at The Point
4.0 star property
8.4 out of 10, Very Good, 531 reviews
"Had a wonderful stay in Orlando. Loved the full kitchen and balcony. Will definitely be back."
The price is $98
includes taxes & fees
$87 per night
Aug 26 - Aug 27
Sonder at The Point
Embassy Suites by Hilton Orlando Downtown
Presidential Suite, 1 King Bed, Non Smoking | View from room
Embassy Suites by Hilton Orlando Downtown
3.5 star property
8.8 out of 10, Excellent, 1,411 reviews
"Our go to for concerts in that area. Everything you need right in the srea."
The price is $162
includes taxes & fees
$144 per night
Aug 4 - Aug 5
Embassy Suites by Hilton Orlando Downtown
Modern Luxury Villa with Everything
Pool
Modern Luxury Villa with Everything
9.8 out of 10, Exceptional, 318 reviews
"We treated our children to our 50th anniversary vacation to have all the Grandkids together. We are scattered about and some haven’t seen one another in a year or more! My Grandkids had the best time, the looks on their faces when they saw the game room and the theatre was priceless!! They were perfect, didn’t fight, literally said they were going to miss one another, asking to stay longer and my youngest Grandson who will be 4 in Aug. asked to stay 5 more days!!! Lol..it was PERFECT!!! My sons...
Modern Luxury Villa with Everything
Florida Hotel & Conference Center in the Florida Mall
Reception
Florida Hotel & Conference Center in the Florida Mall
3.5 star property
9.0 out of 10, Wonderful, 1,517 reviews
"This hotel was great. Just stayed one night while waiting to catch a flight in the morning. It is attached to the mall so lots of food options. It was quiet. You did not have a lot of noise from the mall. Pool was very nice."
The price is $215
includes taxes & fees
$191 per night
Aug 17 - Aug 18
Florida Hotel & Conference Center in the Florida Mall
Quiet Oasis in Lovely Neighborhood
Pool
Quiet Oasis in Lovely Neighborhood
9.8 out of 10, Exceptional, 104 reviews
"This quaint mother in law was clean, quiet and very sufficient for my short trip. Neighborhood was clean and quiet. Owners were very friendly and accommodating. Usage of pool was available though i did not take advantage. Would definitely definitely recommend to a single or couple headed to Orlando. Thank you 😊"
The price is $203
includes taxes & fees
$183 per night
Aug 5 - Aug 6
Quiet Oasis in Lovely Neighborhood
Embassy Suites by Hilton Orlando International Dr Conv Ctr
Indoor pool, outdoor pool, pool umbrellas
Embassy Suites by Hilton Orlando International Dr Conv Ctr
3.5 star property
8.6 out of 10, Excellent, 1,359 reviews
"It is close to everything like attractions and restaurants. "
The price is $104
includes taxes & fees
$92 per night
Aug 18 - Aug 19
Embassy Suites by Hilton Orlando International Dr Conv Ctr
Parc Corniche Condominium Suite Hotel
Exterior
Parc Corniche Condominium Suite Hotel
3.0 star property
7.8 out of 10, Good, 2,075 reviews
"Pool area good and safe for the hole family."
The price is $136
includes taxes & fees
$121 per night
Jul 28 - Jul 29
Parc Corniche Condominium Suite Hotel
WorldQuest Orlando Resort
Superior Suite, 3 Bedrooms, Pool View (3 Bathrooms) | Exterior
WorldQuest Orlando Resort
4.0 star property
8.4 out of 10, Very Good, 3,835 reviews
"This was my second time staying at World Quest and I absolutely love that. You have options of the two bedrooms and two bath, which makes it feel like you are really at home. I know they are just elevators, but I really wish the elevators were more clean and smell better. But I will absolutely stay here again in the future as everybody working there has always been very pleasant and I hope it stays that way"
The price is $332
includes taxes & fees
$295 per night
Jul 28 - Jul 29
WorldQuest Orlando Resort
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See all available properties in Winter Park
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

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Exterior
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
3.5 star property
7.0 out of 10, Good, 515 reviews
"Line for check in was long. I came here years go when it was nick hotel. The property sice then looks a bit more of need for attention and updating. Check in atea had paint vhipping off. Pool area has gates in need of paint "
The price is $143
includes taxes & fees
$133 per night
Jul 30 - Jul 31
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Hyatt Regency Orlando International Airport
Meeting facility
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, 5,156 reviews
"Nice place to stay prior to cruise transportation "
The price is $224
includes taxes & fees
$199 per night
Jul 30 - Jul 31
Hyatt Regency Orlando International Airport
Universal's Endless Summer Resort - Dockside Inn and Suites
2 outdoor pools, pool umbrellas, sun loungers
Universal's Endless Summer Resort - Dockside Inn and Suites
3.0 star property
9.0 out of 10, Wonderful, 5,246 reviews
"Great place to stay when visiting Universal. Dedicated shuttle bus runs throughout the day and night to the park. Pool is beautiful. The 1 BR suite fit 2 adults and 2 teens very comfortably. Kitchenette was awesome. Room was bright and airy and very clean."
The price is $143
includes taxes & fees
$127 per night
Aug 25 - Aug 26
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 private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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.

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 low season months. For more hustle and bustle, you may prefer to visit Winter Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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. 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 near the airport 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. You and your friends and family can relax into your vacation with amenities like a spa tub.

How many vacation rentals are there in Winter Park?

Expedia has 75 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 Alfond Swimming Pool 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.

Recent reviews of Winter Park properties
Expedia verified reviews

Avanti International Resort

Avanti International Resort

5/5 Excellent
"We enjoyed our stay and utilzed the fitness room and pool the most! We walked to dinner and felt safe in the area!!!"
A verified traveler stayed at Avanti International Resort
Posted 14 hours ago
Avanti International Resort

Winter Park Vacation Rental Travel Info

Number of vacation rentals
75
Popular accommodation
Winter Park private vacation homes
Known landmarks
Orlando Science Center, Church Street Station and Orlando Museum of Art
International airport
Orlando, FL (MCO-Orlando Intl.)