Winter Springs, FL Vacation Homes from AED 596

Winter Springs Vacation Homes
Florida
United States of America
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Our top choices for Winter Springs vacation homes

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

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

A covered patio area with a foosball table, chairs, and a dining table.

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

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 AED 479

AED 479

AED 884 total

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 AED 441

AED 441

AED 1,188 total

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.

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.

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 AED 514

AED 514

AED 1,191 total

includes taxes & fees

1 Nov - 2 Nov

Welcoming 2-bedroom house with AC in charming Sanford

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

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

A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.

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

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.

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 curved driveway leading to a building with palm trees and a flag.

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

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.

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.

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 AED 271

AED 271

AED 1,121 total

includes taxes & fees

2 Nov - 3 Nov

Home Sweet Home

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.

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

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 AED 380

AED 380

AED 427 total

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 modern kitchen with a wooden ceiling, a brick wall, and a flat-screen TV above the fireplace.

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.

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 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 wicker outdoor table and chairs set on a tiled patio with a wooden fence in the background.

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

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 AED 215

AED 215

AED 596 total

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.

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

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

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 AED 918

AED 918

AED 1,102 total

includes taxes & fees

1 Nov - 2 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 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.

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

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 AED 430

AED 430

AED 1,286 total

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.

A bathroom with a sink, mirror, toilet, and striped shower curtain.

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

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

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.

The price is AED 643

AED 643

AED 1,542 total

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.

A living room with a sofa, a coffee table, a TV, a dining table with chairs, and a view of the outdoors.

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

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 AED 808

AED 808

AED 1,719 total

includes taxes & fees

1 Nov - 2 Nov

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 kitchen with a central island, wooden bar stools, stainless steel appliances, and a unique ceiling light fixture.

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

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

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 AED 1,451

AED 1,451

AED 2,622 total

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

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

A modern bathroom with a glass-enclosed shower, a white sink, and a toilet.

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 AED 298

AED 298

AED 667 total

includes taxes & fees

1 Dec - 2 Dec

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.

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

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

A poolside area with a wooden pergola, lounge chairs, and a potted plant.

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 traveler

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 modern kitchen with stainless steel appliances, a dishwasher, and a herringbone-patterned backsplash.

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

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

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 AED 329

AED 329

AED 875 total

includes taxes & fees

1 Dec - 2 Dec

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

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

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.

PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark

A swimming pool with a covered patio area, chairs, and a view of the sunset.

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

A bedroom with a bed, bedside tables, a chair, a desk, and a wardrobe.

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

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 AED 459

AED 459

AED 1,070 total

includes taxes & fees

28 Nov - 29 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

Wingate by Wyndham - Orlando International Airport

8/10 Good

"It was a In-N-Out situation when I got there. 10 minutes later I was already on my way with my Venom."

Edwin J 1-night trip

Posted 1 hour ago

Wingate by Wyndham - Orlando International Airport

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 3 hours ago

DoubleTree by Hilton at the Entrance to Universal Orlando

Spark by Hilton Orlando near Universal

10/10 Excellent

"Everything was well organized. Room was very clean. Also, it's was so close to universal studios"

Pablo 3-night trip

Posted 7 hours ago

Spark by Hilton Orlando near Universal

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 8 hours ago

Coco Key Hotel & Water Park Resort

Universal's Helios Grand Hotel, a Loews Hotel

10/10 Excellent

"Would you like to stay near a theme park without it feeling like a theme park hotel? Then Helios is for you."

Kent 2-night trip

Posted 8 hours ago

Universal's Helios Grand Hotel, a Loews Hotel

Avanti International Resort

10/10 Excellent

"Muy bueno"

Irmarie 4-night trip

Posted 12 hours ago

Avanti International Resort

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 14 hours ago

Rosen Inn International

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 22 hours ago

Universal's Terra Luna Resort

Search Vacation Homes in Winter Springs

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Springs vacation 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 vacation rentals that suit your style

Top Winter Springs Hotel Reviews

Wingate by Wyndham - Orlando International Airport