Winter Springs Holiday Homes from £106: Search Holiday Homes in Winter Springs

Winter Springs Holiday Homes
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Our top choices for Winter Springs holiday homes

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

A dining area with a table and chairs, a chandelier, and a large abstract painting on the wall.

A living room with a sectional sofa, a coffee table, a ceiling fan, and a wall art piece.

A kitchen with white cabinets, a microwave, a gas stove, and a blender. There is a blue rug on the floor.

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)

9.8/10

Exceptional

(58 reviews)

"Everything about the house was great. Great house for the price!"

Charles T.

The price is £194

£194

includes taxes & fees

2 Nov - 3 Nov

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

2. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families

Casselberry

9.2 out of 10, Wonderful, (49 reviews)

9.2/10

Wonderful

(49 reviews)

"We had a great time at this property and it met all of our expectations."

lisa b.

The price is £245

£245

includes taxes & fees

2 Nov - 3 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.

A hotel room with two single beds, a desk with a chair, a large mirror, and a ceiling fan.

A house with a front yard, surrounded by trees and plants.

An outdoor seating area with a view of a sunset.

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)

10/10

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."

Aimee B.

The price is £238

£238

includes taxes & fees

30 Nov - 1 Dec

Welcoming 2-bedroom house with AC in charming Sanford

A compact kitchen with white cabinets, a built-in oven, and a ceiling fan.

A room with wooden paneling, a television, a bed, a desk, a chair, and a guitar hanging on the wall.

A house with a covered porch, a brick section, and a garage door.

A covered outdoor gym with a bench press, dumbbells, and weight plates.

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)

8.6/10

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. "

Barbara R.

The price is £151

£151

includes taxes & fees

10 Nov - 11 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.

A covered outdoor seating area with white chairs and a table, surrounded by decorative metal railings and a view of a street with palm trees.

A living room with a flat-screen TV mounted on the wall, a fireplace, and a chandelier.

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)

9.0/10

Wonderful

(23 reviews)

"Host responded quickly to our texts.Location was excellent for our needs."

Angie Y.

The price is £156

£156

includes taxes & fees

9 Nov - 10 Nov

Renovated Peaceful Luxury Walk to Mall Park Publix

A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

A spacious living area with a sofa, a coffee table, and a dining table in the background.

A dining area with a wooden table set for four, a refrigerator, and a kitchen with a tiled backsplash and wooden cabinets.

A bedroom with a bed, a TV mounted on the wall, a dresser, and a potted plant.

6. Home Sweet Home

Home Sweet Home

Sanford

9.4 out of 10, Exceptional, (33 reviews)

9.4/10

Exceptional

(33 reviews)

"Second time to stay at property and it was ideal. Clean, comfortable and easy"

Aimee B.

The price is £240

£240

includes taxes & fees

2 Nov - 3 Nov

Home Sweet Home

A modern living room with a flat-screen TV mounted on a white console, surrounded by potted plants and decorative vases.

A building with a flat roof, a number '1051' on the side, and a paved driveway leading to the entrance.

A bedroom with a bed, a flat-screen TV, a ceiling fan, a door leading to a bathroom, and a mirror.

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 £87

£87

includes taxes & fees

14 Nov - 15 Nov

Accessible Orlando Retreat With Jacuzzi and Shared Pool

A modern kitchen with white cabinets, a wooden dining table, and a hanging light fixture.

A spacious living room with a sofa, coffee table, and yellow armchair. A kitchen is visible in the background.

A spacious living room with a fireplace, a large window, and a wooden ceiling.

An outdoor seating area with Adirondack chairs and a white sofa, surrounded by lush greenery and trees.

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)

9.8/10

Exceptional

(130 reviews)

"The property was very well located and convenient to many restaurants. Lovely back yard."

Sandra F.

The price is £230

£230

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.

A beige sofa with two blue cushions in a room with patterned wallpaper and a window with blinds.

A modern office space with a flat-screen TV mounted on the wall displaying various apps and channels. There is a desk with a chair, a refrigerator, a microwave, and a trash bin.

A modern dining area with a glass table and two blue chairs, a painting on the wall, and a patterned wall behind a window.

9. Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀

Orlando

8.8 out of 10, Excellent, (20 reviews)

8.8/10

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 "

Robin R.

The price is £152

£152

includes taxes & fees

13 Nov - 14 Nov

Sunshine Escape Guesthouse ☀

A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

A single-story house with a front yard, a driveway leading to the entrance, and a small porch area.

A bedroom with a bed, a desk, a chair, and a window with blinds.

A compact bathroom with a shower, toilet, and sink.

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)

10/10

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"

Hannah F.

The price is £231

£231

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.

A conference room with a long table, three black leather chairs, white cabinets with black handles, and a chandelier.

A modern living room with a dark grey sectional sofa, a wooden floor, and a potted plant in the foreground.

A dining area with a wooden table, black chairs, a ceiling fan, and a door with a wooden panel.

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)

9.6/10

Exceptional

(28 reviews)

"Beautiful place to stay near the airport "

Rodney

The price is £254

£254

includes taxes & fees

4 Nov - 5 Nov

Tranquil 3-bedroom house in Sanford with AC, WiFi

A living room with a sofa, coffee table, and decorative wall art.

A bedroom with a bed, a ceiling fan, a window with blinds, a nightstand with a lamp, and a rug.

A closet with shelves labeled for different types of bedding and towels.

A modern kitchen with white cabinets, a dining area with a wooden table, and a view of the living room through an archway.

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)

9.6/10

Exceptional

(5 reviews)

"Nice and roomy!"

Ashley C.

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.

A modern kitchen with blue cabinets, a large island, a dining area, and a view of the outdoors.

A living room with a sofa, coffee table, TV, and framed artwork on the walls.

A dining area with a table set for four, a sofa, and a coffee table in a room with white walls and a large window.

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)

9.6/10

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!"

Miriam R.

The price is £342

£342

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.

A modern living room with a fireplace, a dining area, and a kitchen with wooden cabinets.

A modern kitchen with a marble island, stainless steel appliances, and a large window providing natural light.

A modern dining area with a wooden table, white chairs, and a decorative centerpiece.

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)

10/10

Exceptional

(8 reviews)

"Clean house, good location to where we wanted to be!"

Jennifer M.

The price is £537

£537

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.

A kitchen with a refrigerator, microwave, coffee maker, and wall decorations including a clock and motivational quotes.

A bedroom with a bed, a dresser, a television, and a potted plant.

A bedroom with a bed, a desk, a chair, a bedside table, a lamp, a clock, a window, and a painting.

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)

10/10

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."

Kevin G.

The price is £142

£142

includes taxes & fees

3 Nov - 4 Nov

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

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)

9.8/10

Exceptional

(8 reviews)

"Great place to stay. We plan on staying again."

Nancee H.

The price is £106

£106

includes taxes & fees

2 Nov - 3 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.

A living room with a sofa, two armchairs, a coffee table, and a rug. There is a TV stand with electronic devices and a lamp.

A room with a small table, a chair, and a decorative plant arrangement.

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, two chairs, and a door leading to another room.

17. Modern Tropical Pool Home ⭐️

Modern Tropical Pool Home ⭐️

Orlando

9.8 out of 10, Exceptional, (22 reviews)

9.8/10

Exceptional

(22 reviews)

"We had a great stay and communication with Andy was great!! "

Anonymous traveller

The price is £411

£411

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.

A stone pathway leading to a house with a wooden fence and a tree in the background.

A deck with a grill, wooden tables, and a large tree.

A house entrance with a number '855' on the wall, a wooden door, and a view into the interior.

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)

8.6/10

Excellent

(8 reviews)

"It was nice place to stay!"

Jason A.

The price is £185

£185

includes taxes & fees

4 Nov - 5 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.

A living room with a sofa, a dining table with chairs, a ceiling fan, and a door with a window.

A modern kitchen with stainless steel appliances, a dining area with a table and chairs, and a painting on the wall.

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)

10/10

Exceptional

(4 reviews)

"Nice place , will book again "

Kadijah J.

The price is £328

£328

includes taxes & fees

5 Nov - 6 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.

An aerial view of a modern building with a large glass-enclosed swimming pool, multiple roof sections, and surrounding green lawns.

An outdoor patio area with a round table and six chairs.

A kitchen area with a coffee bar sign, a microwave, and a coffee machine.

20. Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis

Union Park

9.8 out of 10, Exceptional, (28 reviews)

9.8/10

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!"

Amy M.

The price is £228

£228

includes taxes & fees

11 Nov - 12 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

Wyndham I-Drive Avanti Resort & Conference Center

10/10 Excellent

"Clean room"

Kritzia 3-night trip

Posted less than an hour ago

Wyndham I-Drive Avanti Resort & Conference Center

Coco Key Hotel & Water Park Resort

10/10 Excellent

"I loved how the people working there are super accommodating and also the shuttle to and from the parks are so convenient. If you also like walking, you can walk to CityWalk. There are sidewalks"

Nicholas 4-night trip

Posted 1 hour ago

Coco Key Hotel & Water Park Resort

Avanti International Resort

10/10 Excellent

"Muy bueno"

Irmarie 4-night trip

Posted 4 hours ago

Avanti International Resort

Hyatt Regency Orlando International Airport

8/10 Good

"Free"

Eduardo 1-night trip

Posted 6 hours ago

Hyatt Regency Orlando International Airport

Rosen Inn International

10/10 Excellent

"The room was great for the price. The personnel were very nice and helpful. The Hotel is really close to Universal Orlando and the other parks."

Roger 2-night trip

Posted 7 hours ago

Rosen Inn International

Universal's Helios Grand Hotel, a Loews Hotel

10/10 Excellent

"Amazing location, rooms, restaurant, staff pool, everything was perfect."

Erick 2-night trip

Posted 8 hours ago

Universal's Helios Grand Hotel, a Loews Hotel

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Nice place ……………………………….."

kevin 3-night trip

Posted 10 hours ago

DoubleTree by Hilton at the Entrance to Universal Orlando

Universal's Terra Luna Resort

8/10 Good

"There were kids running up and down the halls all night and the room walls are paper thin plus the upstairs guest were extremely loud, aside from that the stay was pleasant"

Margarita 3-night trip

Posted 14 hours ago

Universal's Terra Luna Resort

Find out more about Winter Springs

Winter Springs Holiday Homes information

Number of reviews	355
Accommodation	1457 Holiday Homes
Lowest Price	£106
Highest Price	£537

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Winter Springs on Expedia.com

Search Holiday Homes in Winter Springs

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Springs holiday homes

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

2. Florida Vacation with pool fun for families

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

4. Peaceful Private Gated Patio Walk to Mall Publix

5. Renovated Peaceful Luxury Walk to Mall Park Publix

6. Home Sweet Home

7. Accessible Orlando Retreat With Jacuzzi and Shared Pool

8. A Home Where Eclectic Luxury Meets Affordability

9. Sunshine Escape Guesthouse ☀

10. Spacious 5-bedroom house in gorgeous Winter Park

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

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

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

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

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

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

17. Modern Tropical Pool Home ⭐️

18. Modern Oasis in Orlando | Private Yard | Cabana

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

20. Spacious & Private Guest Pool House Oasis

Find holiday rentals that suit your style

Top Winter Springs Hotel Reviews

Wyndham I-Drive Avanti Resort & Conference Center

Find out more about Winter Springs

Winter Springs Holiday Homes information

Explore a world of travel with Expedia