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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winter Springs vacation homes

A modern kitchen with a microwave, coffee maker, and potted plants. There is a seating area with a sofa and a coffee table.

1. The Longwood Escape • Modern Private Guesthouse Near Orlando

The Longwood Escape • Modern Private Guesthouse Near Orlando
Longwood
The price is ￥13,046
￥25,326 total
includes taxes & fees
Nov 16 - Nov 17
The Longwood Escape • Modern Private Guesthouse Near Orlando
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

2. 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, (58 reviews)
"Everything about the house was great. Great house for the price!"
United States
Charles T.
The price is ￥20,562
￥37,905 total
includes taxes & fees
Nov 2 - Nov 3
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Private kitchen

3. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.2 out of 10, Wonderful, (49 reviews)
"Good location for shops and food etc. quiet neighborhood and host was very nice."
United States
Anonymous traveler
The price is ￥18,907
￥50,955 total
includes taxes & fees
Nov 2 - Nov 3
Florida Vacation with pool fun for families
A compact kitchen with white cabinets, a built-in oven, and a ceiling fan.

4. 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 ￥14,039
￥29,086 total
includes taxes & fees
Nov 3 - Nov 4
Peaceful Private Gated Patio Walk to Mall Publix
A shower with a glass door, a handheld showerhead, and a towel rack.

5. Renovated Peaceful Luxury Walk to Mall Park Publix

Renovated Peaceful Luxury Walk to Mall Park Publix
Altamonte Springs
9.0 out of 10, Wonderful, (23 reviews)
"Host responded quickly to our texts.Location was excellent for our needs."
United States
Angie Y.
The price is ￥15,173
￥30,513 total
includes taxes & fees
Nov 9 - Nov 10
Renovated Peaceful Luxury Walk to Mall Park Publix
A modern kitchen with white cabinetry, a central island with bar stools, a built-in microwave, and a window with a view.

6. Welcoming 2-bedroom house with AC in charming Sanford

Welcoming 2-bedroom house with AC in charming Sanford
Sanford
10.0 out of 10, Exceptional, (5 reviews)
"Charming and beautifully decorated. The home was so comfortable and was well stocked with everything we could have needed. The backyard was awesome with so many fun things. Would stay again."
United States
Aimee B.
The price is ￥22,058
￥49,505 total
includes taxes & fees
Nov 2 - Nov 3
Welcoming 2-bedroom house with AC in charming Sanford
Private kitchen

7. Accessible Orlando Retreat With Jacuzzi and Shared Pool

Accessible Orlando Retreat With Jacuzzi and Shared Pool
2.0 star property
Goldenrod
The price is ￥16,292
￥18,328 total
includes taxes & fees
Nov 3 - Nov 4
Accessible Orlando Retreat With Jacuzzi and Shared Pool
A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

8. Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (33 reviews)
"Second time to stay at property and it was ideal. Clean, comfortable and easy"
United States
Aimee B.
The price is ￥11,628
￥48,095 total
includes taxes & fees
Nov 2 - Nov 3
Home Sweet Home
A modern kitchen with white cabinets, a wooden dining table, and a hanging light fixture.

9. A Home Where Eclectic Luxury Meets Affordability

A Home Where Eclectic Luxury Meets Affordability
Altamonte Springs
9.8 out of 10, Exceptional, (130 reviews)
"The property was very well located and convenient to many restaurants. Lovely back yard."
United States
Sandra F.
The price is ￥19,853
￥46,405 total
includes taxes & fees
Nov 16 - Nov 17
A Home Where Eclectic Luxury Meets Affordability
A modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

10. Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀
Orlando
8.8 out of 10, Excellent, (20 reviews)
"The location worked perfect for our needs in a quiet and safe area. The host was very pleasant and we had a wonderful experience dealing with him and any concerns were met and promptly taken care of. We would definitely stay there again "
United States
Robin R.
The price is ￥9,217
￥25,554 total
includes taxes & fees
Nov 2 - Nov 3
Sunshine Escape Guesthouse ☀
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

11. Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (5 reviews)
"Rented this property for a friend's engagement party and it worked super well. Host was super nice and great with communication"
United States
Hannah F.
The price is ￥39,390
￥47,268 total
includes taxes & fees
Nov 2 - Nov 3
Spacious 5-bedroom house in gorgeous Winter Park
A modern kitchen with a central island, a dining area with a sofa and coffee table, and a large window providing a view.

12. Modern Oasis in Orlando | Private Yard | Cabana

Modern Oasis in Orlando | Private Yard | Cabana
Fairview Shores
8.6 out of 10, Excellent, (8 reviews)
"It was nice place to stay!"
United States
Jason A.
The price is ￥12,756
￥37,414 total
includes taxes & fees
Nov 4 - Nov 5
Modern Oasis in Orlando | Private Yard | Cabana
A kitchen with wooden flooring, green cabinets, a central island, and a microwave.

13. Oviedo Charmer - Heated Pool - Close to everything

Oviedo Charmer - Heated Pool - Close to everything
Oviedo
9.2 out of 10, Wonderful, (44 reviews)
"We absolutely loved our stay at the Oviedo Charmer. "
United States
Nichole L.
The price is ￥29,331
￥65,497 total
includes taxes & fees
Nov 10 - Nov 11
Oviedo Charmer - Heated Pool - Close to everything
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

14. 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 place to stay near the airport "
United States
Rodney
The price is ￥18,435
￥55,468 total
includes taxes & fees
Nov 2 - Nov 3
Tranquil 3-bedroom house in Sanford with AC, WiFi
A front door with a glass panel, a wreath, and a doormat with a welcoming message.

15. Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!

Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
College Park
10.0 out of 10, Exceptional, (3 reviews)
"Quiet location, easy access to many amenities.Host genuinely cares about the clienteles well being and that needs are accommodated for if required."
Canada
Kevin G.
The price is ￥11,384
￥27,994 total
includes taxes & fees
Nov 3 - Nov 4
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
A modern bathroom with a wooden vanity, a round mirror, and a potted plant.

16. Top 1% Modern Japandi Retreat - Jacuzzi No Fee

Top 1% Modern Japandi Retreat - Jacuzzi No Fee
Winter Park
10.0 out of 10, Exceptional, (8 reviews)
"Clean house, good location to where we wanted to be!"
United States
Jennifer M.
The price is ￥62,236
￥107,424 total
includes taxes & fees
Nov 22 - Nov 23
Top 1% Modern Japandi Retreat - Jacuzzi No Fee
Private kitchen

17. Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Apopka
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay. We plan on staying again."
United States
Nancee H.
The price is ￥10,919
￥19,493 total
includes taxes & fees
Nov 2 - Nov 3
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
A bedroom with a bed, bedside table, lamp, TV, fireplace, and a window with curtains.

18. Holiday Home for 10 • Fenced Yard, Pets Welcome, 35 Min to Orlando

Holiday Home for 10 • Fenced Yard, Pets Welcome, 35 Min to Orlando
Sanford
9.6 out of 10, Exceptional, (21 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 ￥34,663
￥71,217 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Home for 10 • Fenced Yard, Pets Welcome, 35 Min to Orlando
A bedroom with a bed, nightstands, a desk, and a chair.

19. 1x1 Guest Suite 10 minutes from UCF

1x1 Guest Suite 10 minutes from UCF
Union Park
9.4 out of 10, Exceptional, (8 reviews)
"The room was clean, quiet and very convenient. It is more spacious than what it looks in photos, a nice alternative to a hotel room. Parking was easy and the area feels safe. "
United States
Michael
The price is ￥7,386
￥16,403 total
includes taxes & fees
Nov 3 - Nov 4
1x1 Guest Suite 10 minutes from UCF
A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

20. CUTE and COZY studio w/ jacuzzi!

CUTE and COZY studio w/ jacuzzi!
Azalea Park
8.6 out of 10, Excellent, (10 reviews)
"This cute lil place is perfect for a few nights for one person or a couple. It’s quiet, private and safe, and appointed with everything you need. The bed is comfy and the coffee was great. "
United States
Lindsay W.
The price is ￥9,961
￥26,977 total
includes taxes & fees
Nov 2 - Nov 3
CUTE and COZY studio w/ jacuzzi!
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

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

10/10 Excellent
"Ubicación.Limpieza"
Christian Omar Gonzalez 4-night trip
Posted less than an hour ago
Spark by Hilton Orlando near Universal

Find out more about Winter Springs

Winter Springs Vacation Homes information

Number of reviews
405
Accommodation
1464 Vacation Homes
Lowest Price
￥16,403
Highest Price
￥107,424