Winter Park Vacation Rentals

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Vacation Rentals in Winter Park

Meeting facility
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4824)
"Great place and location the elevator is little slow. "
The price is $209
$235 total
includes taxes & fees
May 27 - May 28
Hyatt Regency Orlando International Airport
Outdoor pool, pool umbrellas, sun loungers
Avanti International Resort
3.0 star property
7.6 out of 10, Good, (2066)
"I’d definitely stay there again"
The price is $73
$100 total
includes taxes & fees
May 27 - May 28
Avanti International Resort
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, (7194)
"They need to communicate better about the parking. I had to park far away and walk to my building. They did not tell me where I should park, and I finally had to go ask. Then they told me where to park and it was not even close to the building I was staying in!!"
The price is $144
$188 total
includes taxes & fees
May 20 - May 21
Lake Buena Vista Resort Village & Spa
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Water park
CoCo Key Hotel and Water Resort 
3.5 star property
7.4 out of 10, Good, (3737)
"My family and I stayed here three years ago and this past week. Nothing has changed and that is a good thing! The staff is kind and attentive. The hotel is clean and the landscaping is beautiful. They even delivered a microwave to our room at midnight so I could heat up my pizza. For the price, you cannot get better! "
The price is $62
$116 total
includes taxes & fees
May 19 - May 20
CoCo Key Hotel and Water Resort 
Outdoor pool, a heated pool, pool umbrellas, sun loungers
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
3.5 star property
8.6 out of 10, Excellent, (3125)
"Holiday Inn was fantastic! From the front desk to the room, everything was wonderful! "
The price is $67
$106 total
includes taxes & fees
May 27 - May 28
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
Terrace/patio
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
3.0 star property
7.0 out of 10, Good, (2420)
"The view of the big lake was Beautiful. The breakfast options needs work."
The price is $122
$137 total
includes taxes & fees
May 19 - May 20
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Property entrance
The View Studio Suites and Event Venue
3.5 star property
8.4 out of 10, Very Good, (187)
"Very nice staff and people working in the hotel, just a sketchy location with weird people around, but that is to be expected when you stay in the epicenter of a city. We found a bug in our room and they immediately relocated us to another room free of charge which was very nice. Overall a good experience"
The price is $70
$79 total
includes taxes & fees
May 19 - May 20
The View Studio Suites and Event Venue
2 outdoor pools, a heated pool, pool umbrellas, sun loungers
Floridays Resort Orlando
3.5 star property
8.6 out of 10, Excellent, (10670)
"Good property. Nearby Vineland outlet and other abundant shopping options. "
The price is $139
$191 total
includes taxes & fees
May 19 - May 20
Floridays Resort Orlando
Terrace/patio
Holiday Inn & Suites Across From Universal Orlando, an IHG Hotel
3.0 star property
7.0 out of 10, Good, (558)
"All staff were friendly. Air conditioning was poor making hotel and room very warm."
The price is $71
$102 total
includes taxes & fees
May 27 - May 28
Holiday Inn & Suites Across From Universal Orlando, an IHG Hotel
Lobby
Embassy Suites by Hilton Orlando International Dr ICON Park
3.5 star property
8.6 out of 10, Excellent, (1481)
"They always brought up everything we needed. Very accommodating. "
The price is $100
$113 total
includes taxes & fees
May 27 - May 28
Embassy Suites by Hilton Orlando International Dr ICON Park
Pillowtop beds, in-room safe, desk, blackout drapes
Wingate by Wyndham - Orlando International Airport
3.0 star property
8.8 out of 10, Excellent, (3969)
"Great hospitality. Clean and nice location. "
The price is $84
$94 total
includes taxes & fees
May 19 - May 20
Wingate by Wyndham - Orlando International Airport
The Club House | Individually decorated, individually furnished, laptop workspace
Orlando Lakefront Tiny House Community
4.5 star property
9.2 out of 10, Wonderful, (138)
"Great location. Very cozy and fun."
The price is $72
$155 total
includes taxes & fees
May 21 - May 22
Orlando Lakefront Tiny House Community
Outdoor pool
The Point Hotel & Suites
3.5 star property
8.0 out of 10, Very Good, (2955)
"Great Place in a great location. Great Staff that help with any needs in a timely manner"
The price is $93
$117 total
includes taxes & fees
May 19 - May 20
The Point Hotel & Suites
Outdoor pool, pool umbrellas, sun loungers
Sonder at The Point
4.0 star property
8.4 out of 10, Very Good, (489)
"Ótimo hotel indico, excelente atendimento, pessoal Cortez."
The price is $209
$235 total
includes taxes & fees
Jun 14 - Jun 15
Sonder at The Point
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, (1697)
"everything is excellent"
The price is $144
$163 total
includes taxes & fees
Jun 2 - Jun 3
Embassy Suites by Hilton Orlando Lake Buena Vista South
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, (1331)
"Nice clean comfortable "
The price is $93
$104 total
includes taxes & fees
May 26 - May 27
Embassy Suites by Hilton Orlando International Dr Conv Ctr
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, (1356)
"Management went above & Beyond."
The price is $169
$190 total
includes taxes & fees
May 26 - May 27
Embassy Suites by Hilton Orlando Downtown
Reception
Florida Hotel & Conference Center in the Florida Mall
3.5 star property
9.0 out of 10, Wonderful, (1451)
"The hotel is beautiful. The location is super. It is very clean and everyone was very helpful and friendly. From the beautiful ladies at reception to equally beautiful lady that cleaned the room. It is certainly my go to when in the Orlando area"
The price is $143
$184 total
includes taxes & fees
Jun 9 - Jun 10
Florida Hotel & Conference Center in the Florida Mall
Pool
Modern Luxury Villa with Everything
9.8 out of 10, Exceptional, (294)
"Absolutely great the area is Well kept ! Family friendly and great location !!!! We had an amazing time !!!"
Modern Luxury Villa with Everything
Pool
Quiet Oasis in Lovely Neighborhood
9.8 out of 10, Exceptional, (95)
"Pasamos unos dias incredibles y el lugar y la zona muy tranquila ,se los recomiendo"
The price is $90
$203 total
includes taxes & fees
Jun 13 - Jun 14
Quiet Oasis in Lovely Neighborhood
Don't see what you're looking for?
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.

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.)

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

Front of property - evening/night
DoubleTree by Hilton Hotel Orlando at SeaWorld
4.0 star property
7.0 out of 10, Good, (8963)
"Stayed for one night post cruise to have a day at SeaWorld with 3 littles. The location was so very convenient to get to SeaWorld. We will park at the park but there is a walkway to SeaWorld from the hotel property. I did not give high ratings because I do think it could have been a little more well kept. The property wasn’t as well kept as i anticipated the room was not as clean as i had hoped but overall it was a great choice for my family to stay for one evening. The staff were very nice at...
The price is $76
$113 total
includes taxes & fees
May 27 - May 28
DoubleTree by Hilton Hotel Orlando at SeaWorld
Meeting facility
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4824)
"Great place and location the elevator is little slow. "
The price is $209
$235 total
includes taxes & fees
May 27 - May 28
Hyatt Regency Orlando International Airport
Outdoor pool
DoubleTree by Hilton at the Entrance to Universal Orlando
4.0 star property
8.4 out of 10, Very Good, (6372)
"Hotel was very nice and in a convenient area with restaurants and convenience stores close by like Walgreens. My neighbors were so roust but that’s not the hotels fault. "
The price is $101
$114 total
includes taxes & fees
May 27 - May 28
DoubleTree by Hilton at the Entrance to Universal Orlando
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 $62 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 73 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
"I’d definitely stay there again"
A verified traveler stayed at Avanti International Resort
Posted 17 hours ago
Avanti International Resort