
Vacation rentals near Winter Park Tennis Center
We found 10,235 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals within easy reach of Winter Park Tennis Center that can be your home away from home. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the best amenities for spending time at your vacation home, which might include WiFi and a pool. No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Winter Park Tennis Center
Showing deals for:Nov 14 - Nov 21
Image gallery for Escape to Paradise!Luxury Waterfront Heated Pool House in Tranquil Neighborhood!

9.89.8 out of 10 rating
Exceptional
(20 reviews)
Escape to Paradise!Luxury Waterfront Heated Pool House in Tranquil Neighborhood!
Kissimmee, FL
19% off
Price is CA $254
CA $254
CA $2,391 total
CA $2,391 total
includes taxes & fees
Image gallery for Water Lovers Retreat

1010 out of 10 rating
Exceptional
(107 reviews)
Water Lovers Retreat
Sanford, FL
5% off
Price is CA $220
CA $220
CA $2,244 total
CA $2,244 total
includes taxes & fees
Image gallery for 14 Bedroom mansion that sleeps 40 people. Host your wedding reception here

9.89.8 out of 10 rating
Exceptional
(27 reviews)
14 Bedroom mansion that sleeps 40 people. Host your wedding reception here
Kissimmee, FL
10% off
Price is CA $1,113
CA $1,113
CA $10,676 total
CA $10,676 total
includes taxes & fees
Image gallery for Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly

9.29.2 out of 10 rating
Wonderful
(21 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
10% off
Price is CA $518
CA $518
CA $4,730 total
CA $4,730 total
includes taxes & fees
Image gallery for Relax by the pool at this retreat near parks, kayaking, and downtown.

1010 out of 10 rating
Exceptional
(168 reviews)
Relax by the pool at this retreat near parks, kayaking, and downtown.
Longwood, FL
5% off
Price is CA $94
CA $94
CA $861 total
CA $861 total
includes taxes & fees
Image gallery for Edgewater lake house Sanford/Orlando near SFB

1010 out of 10 rating
Exceptional
(58 reviews)
Edgewater lake house Sanford/Orlando near SFB
Sanford, FL
5% off
Price is CA $241
CA $241
CA $2,270 total
CA $2,270 total
includes taxes & fees
Image gallery for StylishAptWtrGrdnOppLake&Prk&Yrd

9.89.8 out of 10 rating
Exceptional
(11 reviews)
StylishAptWtrGrdnOppLake&Prk&Yrd
Winter Garden, FL
5% off
Price is CA $211
CA $211
CA $1,898 total
CA $1,898 total
includes taxes & fees
Image gallery for Walk into Tropical Paradise - POOL - GYM - HOT TUB

1010 out of 10 rating
Exceptional
(5 reviews)
Walk into Tropical Paradise - POOL - GYM - HOT TUB
Altamonte Springs, FL
10% off
Price is CA $704
CA $704
CA $5,905 total
CA $5,905 total
includes taxes & fees
Image gallery for Upstay - Patio Paradise w Pool Spa Games & TikiBar

8.88.8 out of 10 rating
Excellent
(8 reviews)
Upstay - Patio Paradise w Pool Spa Games & TikiBar
Kissimmee, FL
10% off
Price is CA $1,170
CA $1,170
CA $10,984 total
CA $10,984 total
includes taxes & fees
Image gallery for Spacious Vacation Home 20 min from Theme Parks!

9.29.2 out of 10 rating
Wonderful
(56 reviews)
Spacious Vacation Home 20 min from Theme Parks!
Kissimmee, FL
10% off
Price is CA $236
CA $236
CA $2,287 total
CA $2,287 total
includes taxes & fees
Image gallery for Tiny Farmhouse Haven!

9.69.6 out of 10 rating
Exceptional
(48 reviews)
Tiny Farmhouse Haven!
Apopka, FL
5% off
Price is CA $85
CA $85
CA $807 total
CA $807 total
includes taxes & fees
Image gallery for Upstay Luxury Mansion w Pool, Hot tub and BBQ area

9.69.6 out of 10 rating
Exceptional
(8 reviews)
Upstay Luxury Mansion w Pool, Hot tub and BBQ area
Kissimmee, FL
10% off
Price is CA $1,375
CA $1,375
CA $12,289 total
CA $12,289 total
includes taxes & fees
Image gallery for Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford

9.69.6 out of 10 rating
Exceptional
(23 reviews)
Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
Sanford, FL
10% off
Price is CA $172
CA $172
CA $1,598 total
CA $1,598 total
includes taxes & fees
Image gallery for Mid-Century Modern Gem Near Downtown/Winter Park/Baldwin Park

1010 out of 10 rating
Exceptional
(43 reviews)
Mid-Century Modern Gem Near Downtown/Winter Park/Baldwin Park
Orlando, FL
10% off
Price is CA $327
CA $327
CA $2,954 total
CA $2,954 total
includes taxes & fees
Image gallery for Near Disney and USTA tennis campus - Pool Villa on the Lake - Stunning Views!

9.89.8 out of 10 rating
Exceptional
(62 reviews)
Near Disney and USTA tennis campus - Pool Villa on the Lake - Stunning Views!
Kissimmee, FL
10% off
Price is CA $358
CA $358
CA $3,325 total
CA $3,325 total
includes taxes & fees
Image gallery for SPACIOUS 1 BEDROOM LOFT IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2767

9.49.4 out of 10 rating
Exceptional
(25 reviews)
SPACIOUS 1 BEDROOM LOFT IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2767
Kissimmee, FL
19% off
Price is CA $99
CA $99
CA $1,066 total
CA $1,066 total
includes taxes & fees
Image gallery for Spacious Family Retreat w Pool, BBQ & Ping Pong

8.68.6 out of 10 rating
Excellent
(7 reviews)
Spacious Family Retreat w Pool, BBQ & Ping Pong
Kissimmee, FL
10% off
Price is CA $354
CA $354
CA $3,464 total
CA $3,464 total
includes taxes & fees
Image gallery for Alderwood lake house Sanford/Orlando near SFB

9.89.8 out of 10 rating
Exceptional
(109 reviews)
Alderwood lake house Sanford/Orlando near SFB
Sanford, FL
5% off
Price is CA $228
CA $228
CA $2,159 total
CA $2,159 total
includes taxes & fees
Image gallery for Rare Water Views in Vista Cay Resort | Corner Condo Boasting Stunning Lake Views |Near Epic Universe

9.69.6 out of 10 rating
Exceptional
(92 reviews)
Rare Water Views in Vista Cay Resort | Corner Condo Boasting Stunning Lake Views |Near Epic Universe
Orlando, FL
26% off
Price is CA $336
CA $336
CA $3,376 total
CA $3,376 total
includes taxes & fees
Image gallery for NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry

9.89.8 out of 10 rating
Exceptional
(11 reviews)
NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
Orlando, FL
5% off
Price is CA $225
CA $225
CA $2,019 total
CA $2,019 total
includes taxes & fees
Image gallery for Super fun spacious family home with top amenities | Pool/Spa | Sleeps 24

8.68.6 out of 10 rating
Excellent
(21 reviews)
Super fun spacious family home with top amenities | Pool/Spa | Sleeps 24
Kissimmee, FL
10% off
Price is CA $411
CA $411
CA $4,618 total
CA $4,618 total
includes taxes & fees
Image gallery for Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748
Kissimmee, FL
19% off
Price is CA $99
CA $99
CA $1,066 total
CA $1,066 total
includes taxes & fees
Image gallery for Family Retreat w/ Pool, Lake View & Disney Nearby – 5BR Storey Lake Getaway

1010 out of 10 rating
Exceptional
(13 reviews)
Family Retreat w/ Pool, Lake View & Disney Nearby – 5BR Storey Lake Getaway
Kissimmee, FL
10% off
Price is CA $300
CA $300
CA $2,937 total
CA $2,937 total
includes taxes & fees
Image gallery for OASIS PALM HAVEN – 20 minutes to the Disney/Universal theme Parks

9.69.6 out of 10 rating
Exceptional
(79 reviews)
OASIS PALM HAVEN – 20 minutes to the Disney/Universal theme Parks
Kissimmee, FL
10% off
Price is CA $173
CA $173
CA $1,805 total
CA $1,805 total
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Winter Park Tennis Center
The Ultimate 10,350 sq ft Orlando Estate - Your Private Resort Near Disney
Sleeps 28 · 8 bedrooms · 9+ bathrooms
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Vacation Village at Parkway
Sleeps 8 · 2 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
2,751 reviews(2,751 reviews)
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38
Sleeps 38 · 14 bedrooms · 14+ bathrooms
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Lakeview Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
382 reviews(382 reviews)
Modern Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
432 reviews(432 reviews)
Close to Attractions! Comfy Unit, Pool, Shuttle to Parks, Parking, Breakfast
Sleeps 4 · 1 bedroom · 1 bathroom
6.86.8 out of 10
196 reviews(196 reviews)
Top rated rentals - Winter Park Tennis Center
Home away from home
1010 out of 10
Exceptionalexceptional
149 reviews(149 reviews)
Liz was an amazing host and very easy to communicate with. Quiet and safe neighborhood. Felt like being home while on vacation! Definitely our new go to place while in Florida!
Taylor N.
Stayed Jun 2025
Nice stay
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
The four of us stayed for 3 nights. Check in was easy and place was clean. Very roomy with everything needed for our stay. Close to a Walgreens, and some restaurants. Just across the street from the new Epic park. We had a great stay and next time we are in the area would use again.
Ivan
Stayed May 2025
Great property in Historic District of Sanford
1010 out of 10
Exceptionalexceptional
106 reviews(106 reviews)
A great mix of historic charm with modern conveniences. Very clean and comfortable. Close to restaurants and shops and Lake Munroe.Would definitely recommend and stay here again if possible.
Garry G.
Stayed May 2025
Loved the stay
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Perfect place for our family of nine. Loved it
Stephen C.
Stayed Apr 2025
Family Disney vacation
1010 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
What a fantastic home this is indeed. The host had everything ready, things I didn't know we wanted/needed what a nice touch. From reading all the reviews this place got about how great the host was .. I really wanted to try to pay it back and let him be for the week .. and manage on our own and yet they kindly checked in via verbo. They knew we were having a Disney trip and already had the Disney princess balloons .. kids absolutely loved everything about the house and the Disney parks. Everyone's favorite part of the trip was this beautiful home & our host who was always at the ready . Thank you so very much highly recommended! From a young family of four
Maureen B.
Stayed Feb 2025
Excellent Stay
1010 out of 10
Exceptionalexceptional
229 reviews(229 reviews)
We had a great time at this property. Beds were very comfortable. House was very clean. Had all the amenities we needed. Short drive to Disney. Lots of restaurants close by. Alfredo was a great host. Would stay again next time we are in Orlando.
Laszlo P.
Stayed Feb 2025
Family/Friends Vacation
1010 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
The host was absolutely amazing to work with through the whole process. Location is amazing and the amenities included with staying here are absolutely fantastic! This house was the perfect home away from home for our family/friends vacation!
Leanne H.
Stayed Feb 2025
Mas de una casa regular- un lugar muy especial y muy maravilloso!
1010 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
Heartfelt thanks Jose and Nuria for a beautiful stay in your magnificent and homey Casa Ordoñez. It was lovely to say the least and we had everything we could possibly need for a relaxed and comfortable stay. We appreciate how responsive you were to our questions about the property. It was an added advantage that your location is superb in its proximity to Winter Park Historical Downtown District.
We had a very enjoyable stay and would highly recommend your property to others.
Muchas gracias,
Denise and Jim, Canada
Denise D.
Stayed Aug 2024