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Holiday Homes in Winter Springs

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winter Springs holiday homes

A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

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, (58 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is AU$361
includes taxes & fees
5 Oct - 6 Oct
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Private kitchen

2. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (48 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
Florida Vacation with pool fun for families
A modern kitchen with a central island, white cabinets, a stainless steel refrigerator, and a black and white geometric backsplash.

3. Renovated Peaceful Luxury Walk to Mall Park Publix

Renovated Peaceful Luxury Walk to Mall Park Publix
Altamonte Springs
9.0 out of 10, Wonderful, (22 reviews)
"Host responded quickly to our texts.Location was excellent for our needs."
United States
Angie Y.
The price is AU$275
includes taxes & fees
5 Oct - 6 Oct
Renovated Peaceful Luxury Walk to Mall Park Publix
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 AU$264
includes taxes & fees
5 Oct - 6 Oct
Peaceful Private Gated Patio Walk to Mall Publix
A modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

5. 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 AU$245
includes taxes & fees
11 Oct - 12 Oct
Sunshine Escape Guesthouse ☀
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)
"This was excellent in every way. Beautifully decorated that created a warm atmosphere. Beds were very comfortable. If I’m in the area again, I will definitely stay there."
United States
Debra O.
The price is AU$465
includes taxes & fees
5 Oct - 6 Oct
Welcoming 2-bedroom house with AC in charming Sanford
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a dining area with a glass table and white chairs.

7. River City Retreat

River City Retreat
Sanford
9.6 out of 10, Exceptional, (21 reviews)
"Worked great for our needs!"
United States
Kelley H.
The price is AU$313
includes taxes & fees
6 Oct - 7 Oct
River City Retreat
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)
"The house was perfect for our three night stay. The location was a short distance to all our activities. It was super clean and had very nice updates. The area was quiet and the house very comfortable. If we are in the area again, we’ll definitely stay there again!"
United States
Janice M.
The price is AU$465
includes taxes & fees
19 Oct - 20 Oct
Home Sweet Home
A two-story yellow house with a porch, surrounded by lush greenery and trees.

9. 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, (29 reviews)
"Really cute cottage with charming eclectic style. Stayed with two adults and four teens and everyone had plenty of space with comfortable sleeping. Would absolutely stay again!"
United States
Wendy K.
The price is AU$516
includes taxes & fees
30 Sept - 1 Oct
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

10. 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 AU$516
includes taxes & fees
4 Oct - 5 Oct
Tranquil 3-bedroom house in Sanford with AC, WiFi
A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

11. CUTE and COZY studio w/ jacuzzi!

CUTE and COZY studio w/ jacuzzi!
Azalea Park
8.6 out of 10, Excellent, (10 reviews)
"Pet friendly, all you need for a quick trip to Orlando with a couple and their pet"
United States
Jackson K.
The price is AU$258
includes taxes & fees
30 Sept - 1 Oct
CUTE and COZY studio w/ jacuzzi!
A modern living room with a ceiling fan, a flat-screen TV, and a dining area with a white table and chairs.

12. 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, (5 reviews)
"Our stay here was excellent! We were able to have a birthday party for our one-year-old grandson, turning 2 and it was an awesome day. Everything was perfect, and the host was very generous about giving us a late check out on the day we left. Would LOVE to stay here again in the future! Thank you, Glen!"
United States
t z.
The price is AU$563
includes taxes & fees
7 Oct - 8 Oct
The Canopy on Periwinkle- A Home Away From Home
A bedroom with a bed, bedside table, lamp, TV, fireplace, and a window with curtains.

13. Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10

Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10
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 AU$553
includes taxes & fees
30 Sept - 1 Oct
Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10
Terrace/patio

14. Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.

Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
West Lakes District
10.0 out of 10, Exceptional, (4 reviews)
"Tammie is an amazing host! Super comfy and cute tiny home! Definitely booking again!"
United States
chelsea
The price is AU$194
includes taxes & fees
30 Sept - 1 Oct
Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

15. Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (4 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 AU$492
includes taxes & fees
30 Sept - 1 Oct
Spacious 5-bedroom house in gorgeous Winter Park
A wooden deck with two lounge chairs and a small table, surrounded by lush tropical plants.

16. 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 traveller
The price is AU$563
includes taxes & fees
28 Oct - 29 Oct
Modern Tropical Pool Home ⭐️
A modern kitchen with a central island, a dining area with a sofa and coffee table, and a large window providing a view.

17. 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 AU$357
includes taxes & fees
19 Oct - 20 Oct
Modern Oasis in Orlando | Private Yard | Cabana
Private kitchen

18. 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 AU$192
includes taxes & fees
6 Oct - 7 Oct
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
A bed with white bedding and two blue pillows with a coral reef design, a tall green plant beside the bed, and a window with grey curtains in the background.

19. Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
United States
Matthew
Studio in the heart of Orlando
A front door with a glass panel, a wreath, and a doormat with a welcoming message.

20. 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, (2 reviews)
"Very nice location in a quiet residential neighborhood. There is only street parking but usually plenty of space."
United States
rimma
The price is AU$249
includes taxes & fees
13 Oct - 14 Oct
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
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

Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

10/10 Excellent
"Lo recomiendo,lo mejor fue la piscina"
Suleidy 2-night trip
Posted less than an hour ago
Coco Key Hotel & Water Park Resort

Find out more about Winter Springs

Winter Springs Holiday Homes information

Number of reviews
193
Accommodation
1464 Holiday Homes
Lowest Price
AU$192
Highest Price
AU$563