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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Winter Springs vacation homes

3 bedrooms, desk, iron/ironing board, WiFi (free)

1. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (54 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is ￥20,588
￥40,004 total
includes taxes & fees
Aug 20 - Aug 21
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Coffee/tea maker, fridge, microwave, oven

2. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (44 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is ￥18,931
￥53,859 total
includes taxes & fees
Aug 10 - Aug 11
Florida Vacation with pool fun for families
Coffee/tea maker, fridge, microwave, oven

3. A Home Where Eclectic Luxury Meets Affordability

A Home Where Eclectic Luxury Meets Affordability
Altamonte Springs
9.8 out of 10, Exceptional, (127 reviews)
"The property was very well located and convenient to many restaurants. Lovely back yard."
United States
Sandra F.
The price is ￥19,720
￥48,338 total
includes taxes & fees
Aug 13 - Aug 14
A Home Where Eclectic Luxury Meets Affordability
Private kitchen

4. Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
10.0 out of 10, Exceptional, (2 reviews)
"This property is perfect for a family get together. Very clean and close to so many restaurants and entertainment. The communication the host was great. I would definely stay there again."
United States
Mary Ellen R.
The price is ￥39,440
￥49,852 total
includes taxes & fees
Aug 14 - Aug 15
Cute 5-bedroom house in peaceful Winter Park
Smart TV, fireplace, stereo

5. The Canopy on Periwinkle- A Home Away From Home

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
10.0 out of 10, Exceptional, (3 reviews)
"The home is beautiful!! The place was clean, comfortable, and exactly as described. The host was friendly, responsive, and made everything easy. I would definitely stay here again and recommend it to others."
United States
Breasia J.
The price is ￥38,194
￥73,438 total
includes taxes & fees
Sep 8 - Sep 9
The Canopy on Periwinkle- A Home Away From Home
Dining

6. River City Retreat

River City Retreat
Sanford
9.6 out of 10, Exceptional, (20 reviews)
"Great place and quick, simple check in."
United States
Dennis L.
The price is ￥19,168
￥34,091 total
includes taxes & fees
Aug 16 - Aug 17
River City Retreat
4 bedrooms, desk, iron/ironing board, WiFi (free)

7. Sanford Group Getaway- 4BR/Sleeps 10, Pet Friendly

Sanford Group Getaway- 4BR/Sleeps 10, Pet Friendly
Sanford
9.8 out of 10, Exceptional, (19 reviews)
"Thank you so much we had a wonderful visit and so great to be able to bring our dog he really loved the back yard!"
United States
Miriam R.
The price is ￥34,707
￥63,798 total
includes taxes & fees
Aug 10 - Aug 11
Sanford Group Getaway- 4BR/Sleeps 10, Pet Friendly
Terrace/patio

8. Modern Tropical Pool Home ⭐️

Modern Tropical Pool Home ⭐️
Orlando
9.8 out of 10, Exceptional, (22 reviews)
"We had a great stay and communication with Andy was great!! "
United States
Anonymous traveler
The price is ￥31,180
￥66,512 total
includes taxes & fees
Aug 28 - Aug 29
Modern Tropical Pool Home ⭐️
Pool

9. Breezy Escape in Oviedo

Breezy Escape in Oviedo
Oviedo
10.0 out of 10, Exceptional, (11 reviews)
"Home was beautiful, neighborhood was very nice. Definitely staying again when in the area!"
United States
Jeremy B.
The price is ￥31,552
￥54,112 total
includes taxes & fees
Aug 23 - Aug 24
Breezy Escape in Oviedo
Dining

10. PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark

PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
Orlando
10.0 out of 10, Exceptional, (4 reviews)
"Nice place , will book again "
United States
Kadijah J.
The price is ￥26,622
￥67,853 total
includes taxes & fees
Aug 10 - Aug 11
PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
Coffee/tea maker, fridge, microwave, oven

11. Renovated Peaceful Luxury Walk to Mall Park Publix

Renovated Peaceful Luxury Walk to Mall Park Publix
Altamonte Springs
9.0 out of 10, Wonderful, (20 reviews)
"Host responded quickly to our texts.Location was excellent for our needs."
United States
Angie Y.
The price is ￥13,488
￥30,064 total
includes taxes & fees
Aug 18 - Aug 19
Renovated Peaceful Luxury Walk to Mall Park Publix
3 bedrooms, desk, iron/ironing board, WiFi

12. Tranquil 3-bedroom house in Sanford with AC, WiFi

Tranquil 3-bedroom house in Sanford with AC, WiFi
Sanford
9.6 out of 10, Exceptional, (28 reviews)
"Beautiful home! My friends and I had such an amazing time and I loved the dog bed & bowls for my dog Venus who stayed with us"
United States
Janelle G.
The price is ￥18,458
￥58,220 total
includes taxes & fees
Aug 11 - Aug 12
Tranquil 3-bedroom house in Sanford with AC, WiFi
Coffee/tea maker, fridge, microwave, oven

13. Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (33 reviews)
"Very comfortable and clean home! "
United States
Stacy B.
The price is ￥10,649
￥49,095 total
includes taxes & fees
Aug 11 - Aug 12
Home Sweet Home
Pool

14. Private Luxury Pool / Swim up bar / Smart-home

Private Luxury Pool / Swim up bar / Smart-home
College Park
9.6 out of 10, Exceptional, (83 reviews)
"Best VRBO thus far, the host were great and the smart house offered much more than expected, I’d recommend this house to any family! I’d definitely stay again!"
United States
Dennis P.
Private Luxury Pool / Swim up bar / Smart-home
Dishwasher

15. Peaceful Private Gated Patio Walk to Mall Publix

Peaceful Private Gated Patio Walk to Mall Publix
Altamonte Springs
8.6 out of 10, Excellent, (4 reviews)
"Everything was perfect, clean, and all staff were very polite , friendly and respectful. All were willing to help out, and responded quickly to any and all questions. Thank you again for the nice accommodation. "
United States
Barbara R.
The price is ￥12,779
￥28,953 total
includes taxes & fees
Sep 7 - Sep 8
Peaceful Private Gated Patio Walk to Mall Publix
Exterior

16. Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!

Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Sanford
10.0 out of 10, Exceptional, (27 reviews)
"We absolutely loved this house! So cute and ample space. The outdoor space was so nice to grill and hangout!"
United States
Danielle C.
The price is ￥22,717
￥63,621 total
includes taxes & fees
Aug 10 - Aug 11
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Fridge, microwave, oven, stovetop

17. Stylish & Cozy King Bed Retreat @ Baldwin Park

Stylish & Cozy King Bed Retreat @ Baldwin Park
Orlando
10.0 out of 10, Exceptional, (15 reviews)
"The house was beautiful and the host was very responsive! "
United States
Dawn H.
Stylish & Cozy King Bed Retreat @ Baldwin Park
Coffee/tea maker, fridge, microwave, oven

18. The Villa Orlando@College Park. Sleeps16.

The Villa Orlando@College Park. Sleeps16.
College Park
9.6 out of 10, Exceptional, (25 reviews)
"Great location in College Park neighborhood. Easy walk to shops and restaurants"
United States
Matt P.
The price is ￥39,550
￥73,976 total
includes taxes & fees
Aug 10 - Aug 11
The Villa Orlando@College Park. Sleeps16.
Exterior detail

19. Pet Friendly!✰ Charming home with big patio!

Pet Friendly!✰ Charming home with big patio!
Oviedo
9.8 out of 10, Exceptional, (24 reviews)
"Host was very helpful. It’s a nice place to stay. Very comfortable."
United States
Sandranel B.
The price is ￥18,142
￥55,152 total
includes taxes & fees
Aug 10 - Aug 11
Pet Friendly!✰ Charming home with big patio!
Microwave, oven, stovetop, dishwasher

20. Modern Oasis in Orlando | Private Yard | Cabana

Modern Oasis in Orlando | Private Yard | Cabana
Fairview Shores
8.4 out of 10, Very Good, (7 reviews)
"The appliances are awesome!"
United States
Steven T.
Modern Oasis in Orlando | Private Yard | Cabana
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.
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Top Winter Springs Hotel Reviews

Universal's Loews Sapphire Falls Resort

Universal's Loews Sapphire Falls Resort

10/10 Excellent
"A great location to explore the Universal parks. Hotel is very clean and the team are always so helpful and pleasant. Parking is a bit steep at $36 a day."
Darren 5-night trip
Posted less than an hour ago
Universal's Loews Sapphire Falls Resort

Find out more about Winter Springs

Winter Springs Vacation Homes information

Number of reviews
416
Accommodation
1486 Vacation Homes
Lowest Price
￥28,953
Highest Price
￥73,976