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Vacation rentals in Winter Park, FL and nearby

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All 2,487 Rentals in the Winter Park Area
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From
$107
Per Night
Winter Park
2 Bedrooms, 1 Bathroom, Sleeps 4
43 photos Details Make Enquiry
From
$75
Per Night
Winter Park
1 Bedroom, 1 Bathroom, Sleeps 4
14 photos Details Make Enquiry
From
$426
Per Night
Winter Park
5 Bedrooms, 3 Bathrooms, Sleeps 10
13 photos Details Make Enquiry
Also consider
Luxurious 5 Bedroom Villa on the Glenbrook Resort
5 Bedrooms, sleeps 8
$153 - $211 / night
2-Bedroom @ Cypress Pointe Grande Villas DISNEY
2 Bedrooms, sleeps 6
$281 / night
Upscale Villa - located on DISNEY PROPERTY,
2 Bedrooms, sleeps 8
$281 / night
Serendipity at Indian Creek
5 Bedrooms, sleeps 12
$461 - $557 / night
From
$956
Per Night
Winter Park
5 Bedrooms, 7 Bathrooms, Sleeps 11
30 photos Details Make Enquiry
From
$337
Per Night
Winter Park
8 Bedrooms, 5 Bathrooms, Sleeps 16
17 photos Details Make Enquiry
From
$337
Per Night
Winter Park
8 Bedrooms, 5 Bathrooms, Sleeps 16
17 photos Details Make Enquiry

The following rentals are within 10 kilometres of Winter Park, Florida.

From
$138
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
20 photos Details Reviews (2) Make Enquiry
3 of 5 stars Reviewed 11 June 2014
Booked this via our agent alas a deluxe executive villa, it is indeed very nice but does not seems to have been maintained too well. The patio doors stick, the chair feet are...
5 of 5 stars Reviewed 2 April 2014
We stayed at Autumn Glenn for just a short stay before returning home up North. Chris the owner is wonderful to work with! He was gracious and patient as we had to at the last...
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From
$141
Per Night
Orlando
1 Bedroom, 1 Bathroom, Sleeps 4
9 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 4 May 2014
From the arrival to departure, our stay was a real pleasure. Staff is very welcoming and friendly. Amenities were clean and well maintained. Units are large and very comfortable...
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From
$179
Per Night
Orlando
3 Bedrooms, 4 Bathrooms, Sleeps 8
Bookings
17 photos Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 22 April 2014
Muy bueno si te gusta estar como en casa. Los colchones son muy blandos y seria bastante mejor si le dieran mantenimiento
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From
$128
Per Night
Orlando
4 Bedrooms, 3 Bathrooms, Sleeps 8
45 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 26 August 2014
Spent the last 2 weeks in Villa 513 at Calabay Parc at Tower Lake, Haines City. I can honestly say that this is one of the best villas that we have stayed in (and we have stayed...
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From
$506
Per Night
Orlando
4 Bedrooms, 4 Bathrooms, Sleeps 16
Bookings
17 photos Details Reviews (3) Make Enquiry
2 of 5 stars Reviewed 10 August 2014
Arrived to a very crowded resort and pools! DON'T BE FOOLED...only some units have new appliances and couches etc. I was expecting what I saw in these pictures. The couches are...
5 of 5 stars Reviewed 16 July 2014
This place was clean and updated and with 4 bedrooms there was lots of space. Loved all the jetted tubs and balconies. Very close to all the parks and lots of activities to do...
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From
$371
Per Night
Orlando
5 Bedrooms, 4 Bathrooms, Sleeps 12
Bookings
33 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 9 March 2014
This was an Excellent house we stayed in a few years back for a family vacation. The house was amazing. Very beautiful and comfortable. We all loved it very much and would stay...
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From
$209
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
8 photos Details Reviews (1) Make Enquiry
From
$304
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
20 photos Details Reviews (2) Make Enquiry
From
$562
Per Night
Orlando
4 Bedrooms, 4 Bathrooms, Sleeps 12
17 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 23 July 2014
I have stayed at Rosa Bella with my family and some friends from NY. The property was very spacious, comfortable and very clean. It was the perfect place to relax and enjoy the...
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From
$225
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
24 photos Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 19 August 2013
The Owner was great and easy to work with. The property was very nice and had many amenities (many pools, lazy rivers, waterslides, mini golf, volleyball & gameroom) to please...
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From
$152
Per Night
Orlando
5 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
20 photos Details Reviews (9) Make Enquiry
5 of 5 stars Reviewed 29 January 2014
This was our first time to rent a vacation home and it was just what we hoped for! It offered lots of comfortable bedrooms, 31/2 bathrooms and visiting rooms for great visiting...
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From
$219
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
38 photos Details Reviews (16) Make Enquiry
5 of 5 stars Reviewed 9 September 2014
It´s our 3rd Vacation in this house, because we love it...we feel we are at home. We called it "our Harry Potter House". I have 3 Teenager (15, 14,and 12 years old), 2 children in...
5 of 5 stars Reviewed 4 September 2014
I would highly recommend your beautiful home to everyone. It was exactly as the pictures advertised. Very clean and well equipped with everything you would need in a home away...
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From
$118
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
21 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 25 September 2014
This was the best place our family has ever stayed for our mini weekend staycations in terms of quality and value. It's hard to balance the two but it's a must for us because we...
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From
$134
Per Night
Orlando
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
24 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 21 September 2014
Fantastic villa the location is great, pool not overlooked which is great for disabled quests using the pool. The furniture, cleanliness and decoration through the house is fab...
5 of 5 stars Reviewed 27 August 2014
Very nice house and attention to the details.. I got surprised to see at home many DVD titles, pool toys, kids toys (that really make the difference when not playing at the...
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From
$129
Per Night
Orlando
3 Bedrooms, 4 Bathrooms, Sleeps 6
Bookings
10 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 30 July 2014
Very nice place, less than 5 miles to SeaWorld and Universal Studios. Centraly located to a lot of good food and attractions. Had issue with WiFi but one phone call and Norm was...
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From
$163
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
9 photos Details Reviews (1) Make Enquiry
From
$163
Per Night
Orlando
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
20 photos Details Reviews (10) Make Enquiry
5 of 5 stars Reviewed 22 September 2014
Beautiful villa, spacious and large pool area. Interior decor lovely. So peaceful. Good location, easy to get to shops and restaurants. Would highly recommend
5 of 5 stars Reviewed 26 July 2014
This really is a luxurious villa with all the home comforts you would expect. There were 4 of us staying here which gave us more than enough space. It was great to retreat back to...
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From
$107
Per Night
Orlando
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
11 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 7 July 2014
We stayed in this lovely villa for the July 4th weekend. This was our 1st time staying in a vacation home & what a great experience we had! Smooth transaction.. Wonderful lake...
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From
$89
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
12 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 27 September 2014
We stayed here for 4 nights with some friends, we LOVED the place, it was very clean, it was cozy and there is just simply nothing that we didn't enjoy from it. The condo is very...
3 of 5 stars Reviewed 9 June 2014
If you want a cheep place to stay in the middle of Disney and universal with 2 bedrooms 2 bath and pool it was good Good points View was of fountain in pond Was apt complex so...
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From
$337
Per Night
Orlando
4 Bedrooms, 5 Bathrooms, Sleeps 8
Bookings
50 photos Details Reviews (14) Make Enquiry
5 of 5 stars Reviewed 25 July 2014
Hidden behind a roadside gate is a beautiful, well managed property with five very different suites that are all enchanting. Each suite is private and you feel like you are in...
5 of 5 stars Reviewed 19 April 2014
The owner has created five extraordinarily lovely rooms, each with its own theme and private patio, in a three-acre tropical garden of flowering trees. Her wit and imagination...
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From
$101
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
18 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 12 August 2014
Dear Raul, I would like to thank you for renting your lovely and homely townhouse to my family and I. The townhouse is in ideally located near the outlet, malls and the theme...
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From
$213
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
15 photos Details Reviews (35) Make Enquiry
5 of 5 stars Reviewed 18 August 2014
The apartment's location on Universal Boulevard was just perfect. We didn't want to limit ourselves to Disney and this was located close to International Drive, Universal...
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From
$152
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
35 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 8 September 2014
The condo is absolutely great! I stayed with my wife and 2 children for a week and I cannot be more pleased. In our family scale this is what we were looking for in order of...
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From
$61
Per Night
Orlando
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
11 photos Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 11 July 2014
We were in Orlando for competition at ESPN WWOS. We rented a "deluxe" room 7-nights & paid extra for delux vs standard room only to find at check in that all rooms are...
5 of 5 stars Reviewed 28 May 2014
From first to last contact with Eric the owner of the condo, was first class. We did request the one bedroom condo but this was not available we were offered the 3 bedroom condo...
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From
$96
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
23 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 30 August 2014
The location of your property was excellent. It wasn't too far from Disney. The amenities were great. We loved the pool. Grocery and shopping is nearby. We will definitely...
5 of 5 stars Reviewed 27 August 2014
I am a busy executive in the Music Industry and needed a break from hectic schedule. My wife and I stayed at the "House Near Disney" in July and were pleasantly suprised with how...
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From
$168
Per Night
Orlando
3 Bedrooms, 4 Bathrooms, Sleeps 8
Bookings
45 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 22 January 2014
I was very happy with my stay. It was clean and comfortable. Everything was close by. They kids had a great time as well they loved the pool. I really liked the door lock system...
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From
$96
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
25 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 19 August 2014
Me and my family was surprised when we arrive and saw the condo, with 2 extensive rooms, the kitchen and laundry room as news. My kids onjoyed in the pool, condo is in private...
5 of 5 stars Reviewed 25 April 2014
I was pleasantly surprised to see such a beautiful 2BR/2BA condo with a full kit/LR and DR. It even has a laundry room with washer and dryer. Fully equipped kitchen, I cooked...
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From
$111
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
31 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 17 September 2014
Hi stayed in one of the Hampton oak villas with my partners and 2 kids, great villa not to far out from shops etc... And great resturants. Pool was good and cleaned regularly...
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From
$146
Per Night
Orlando
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
17 photos Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 21 August 2014
A truly exceptional house and if we had lifted and placed it in orlando to meet our holiday needs (theme parks, malls, restos) it woul not have been any better. Coupled with the...
5 of 5 stars Reviewed 27 July 2014
This is a lovely, very spacious house. Plenty of room for 4 adults and 2 kids. Two ensuite bedrooms, plus a further bathroom shared between the 2 kids' rooms. The pool was...
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From
$179
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
39 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 2 January 2014
The accommodations exceeded our expectations. I was very relieved when we opened the door to a clean, beautifully furnished condo. It was wonderful to relax after a hectic day at...
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From
$153
Per Night
Orlando
5 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
24 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 6 August 2014
We have just returned from this beautiful villa. This is our third visit to Florida in five years and first time at this villa, but should we return, we would definately book it...
5 of 5 stars Reviewed 10 March 2014
We spent two weeks in February this spectacular and well-kept villa. The time just flew by while the days we were in amusement parks and shopping. The evenings we relaxed a large...
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From
$90
Per Night
Orlando
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
29 photos Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 9 June 2014
We couldn't be happier with this choice! Very clean and comfortable one-bedroom, with everything provided that you could possibly need. Covered patio looking out over the lake...
5 of 5 stars Reviewed 1 March 2014
Had a great time. couple we rented from made us feel welcome. Nice and relaxing cottage looking out to the lake. It had everything we needed, close to stores and restaurants...
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From
$135
Per Night
Orlando
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
24 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 10 September 2014
We spent 2 brilliant weeks here in early August - weather was perfect, villa was beautiful and a perfect location Children thoroughly enjoyed the pool. Really easy access to all...
5 of 5 stars Reviewed 30 July 2014
This is a great vacation villa with plenty of room for a family of 5 or even more. It was very clean and well maintained. The pool was perfect for kids and adults and a welcome...
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From
$245
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
15 photos Details Reviews (3) Make Enquiry
From
$79
Per Night
Orlando
1 Bedroom, 2 Bathrooms, Sleeps 6
Bookings
21 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 20 August 2014
Great location,friendly front staff,clean and comfortable with lots of parking,what more can you ask for.
4 of 5 stars Reviewed 7 April 2014
We were really happy with this condo. We have two boys (age 12 and 14) who found the bunk beds pretty comfortable (our 14 year old is 6 '). They were disappointed that wi-fi isn't...
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From
$444
Per Night
Orlando
5 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
57 photos Details Reviews (52) Make Enquiry
5 of 5 stars Reviewed 12 October 2014
My family had the pleasure of staying at Serendipity at Indian Creek during the last week of September. It was wonderful! The owners (Ken & Sarah) do not miss any details. The...
5 of 5 stars Reviewed 3 August 2014
We really enjoyed our week at Serendipity. I took my family down to Orlando with my brother and his family. There were 10 of us in total and the house was prefect for our group...
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From
$163
Per Night
Orlando
3 Bedrooms, 4 Bathrooms, Sleeps 10
Booking
37 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 4 August 2014
Stayed there on a weekend with family. Very spacious and luxurious. The condo was spotless and near all attractions. The clubhouse and pool area was amazing and included a bar...
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From
$123
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
24 photos Details Reviews (3) Make Enquiry
3 of 5 stars Reviewed 30 April 2014
The reservation and payment process through Trip Advisor/Flip Key was very confusing. We ended up being billed by FlipKey and also the resort when checking in which tok a few days...
5 of 5 stars Reviewed 18 April 2014
We booked this condo hoping for a place with a little more room than a hotel would provide for our spring break trip. Our kids are older (17, 15 and 11), and we wanted a place...
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Suitability

  • Wheelchair access (194)
  • Elder access (406)
  • Suitable for children (521)
  • Pet friendly (79)
  • Smoking allowed (9)

Amenities

  • Internet (1,618)
  • Air Conditioning (1,356)
  • All pools (757)
  • Public pool (584)
  • Washer/Dryer (577)
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