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Holiday Homes in Winter Springs

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Check prices for these dates

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

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)
"Everything about the house was great. Great house for the price!"
United States
Charles T.
The price is NZ$427
includes taxes & fees
2 Nov - 3 Nov
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
9.2 out of 10, Wonderful, (49 reviews)
"We had a great time at this property and it met all of our expectations."
United States
lisa b.
The price is NZ$573
includes taxes & fees
1 Nov - 2 Nov
Florida Vacation with pool fun for families
A modern kitchen with white cabinetry, a central island with bar stools, a built-in microwave, and a window with a view.

3. 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 NZ$574
includes taxes & fees
1 Dec - 2 Dec
Welcoming 2-bedroom house with AC in charming Sanford
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 NZ$340
includes taxes & fees
3 Nov - 4 Nov
Peaceful Private Gated Patio Walk to Mall Publix
A modern kitchen with a central island, white cabinets, a stainless steel refrigerator, and a black and white geometric backsplash.

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 NZ$342
includes taxes & fees
10 Nov - 11 Nov
Renovated Peaceful Luxury Walk to Mall Park Publix
A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

6. 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 NZ$564
includes taxes & fees
2 Nov - 3 Nov
Home Sweet Home
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 NZ$207
includes taxes & fees
1 Nov - 2 Nov
Accessible Orlando Retreat With Jacuzzi and Shared Pool
A modern kitchen with white cabinets, a wooden dining table, and a hanging light fixture.

8. 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 NZ$518
includes taxes & fees
16 Nov - 17 Nov
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.

9. 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 NZ$288
includes taxes & fees
1 Nov - 2 Nov
Sunshine Escape Guesthouse ☀
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

10. 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 NZ$526
includes taxes & fees
11 Nov - 12 Nov
Spacious 5-bedroom house in gorgeous Winter Park
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

11. 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 NZ$645
includes taxes & fees
1 Nov - 2 Nov
Tranquil 3-bedroom house in Sanford with AC, WiFi
A living room with a sofa, coffee table, and decorative wall art.

12. Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Goldenrod
9.6 out of 10, Exceptional, (5 reviews)
"Nice and roomy!"
United States
Ashley C.
The price is NZ$705
includes taxes & fees
1 Nov - 2 Nov
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
A bedroom with a bed, bedside table, lamp, TV, fireplace, and a window with curtains.

13. 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 NZ$801
includes taxes & fees
1 Dec - 2 Dec
Holiday Home for 10 • Fenced Yard, Pets Welcome, 35 Min to Orlando
A modern bathroom with a wooden vanity, a round mirror, and a potted plant.

14. 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 NZ$1,239
includes taxes & fees
22 Nov - 23 Nov
Top 1% Modern Japandi Retreat - Jacuzzi No Fee
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 NZ$332
includes taxes & fees
3 Nov - 4 Nov
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
Private kitchen

16. 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 NZ$231
includes taxes & fees
17 Nov - 18 Nov
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
A wooden deck with two lounge chairs and a small table, surrounded by lush tropical plants.

17. 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 NZ$1,021
includes taxes & fees
5 Nov - 6 Nov
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.

18. 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 NZ$435
includes taxes & fees
9 Nov - 10 Nov
Modern Oasis in Orlando | Private Yard | Cabana
A modern kitchen with white cabinets, a stainless steel sink, and a dining area with a table and chairs.

19. 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 NZ$768
includes taxes & fees
12 Nov - 13 Nov
PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
A swimming pool with a covered patio area, chairs, and a view of the sunset.

20. Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (28 reviews)
"Super clean, super comfy, super quiet! Well-appointed unit, comfortable bed, crisp linen, great shower. Host was a great communicator and very accommodating. Property is impeccable and the pool is great!"
United States
Amy M.
The price is NZ$496
includes taxes & fees
27 Nov - 28 Nov
Spacious & Private Guest Pool House Oasis
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

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Only stayed there 3 nights but staff were great! Room was clean and definitely big enough!"
Abbey 3-night trip
Posted less than an hour ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Find out more about Winter Springs

Winter Springs Holiday Homes information

Number of reviews
355
Accommodation
1441 Holiday Homes
Lowest Price
NZ$231
Highest Price
NZ$1,239