A greenhouse with hanging flower baskets and ivy-covered walls.

Holiday Homes in Longwood

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Longwood holiday 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 AU$240
includes taxes & fees
28 Sept - 29 Sept
The Longwood Escape • Modern Private Guesthouse Near Orlando

2. The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub

The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
Longwood
8.0 out of 10, Very good, (4 reviews)
"Awesome place to stay! Was well stocked for our big group and plenty of space for everyone to hang out."
United States
Tyler P.
The price is AU$2,731
includes taxes & fees
20 Sept - 21 Sept
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
A modern kitchen with white cabinets, a wooden dining table, and a hanging light fixture.

3. A Home Where Eclectic Luxury Meets Affordability

A Home Where Eclectic Luxury Meets Affordability
Altamonte Springs
9.8 out of 10, Exceptional, (128 reviews)
"We stayed in Altamonte for a family celebration and were looking for a nearby place that could comfortably accommodate five people with three bedrooms — this home was absolutely perfect! The house was spotless, beautifully maintained, and thoughtfully equipped with everything we needed. The host was friendly, responsive, and readily available to answer any questions, which made our stay even more enjoyable."
United States
Brenda N.
The price is AU$432
includes taxes & fees
23 Sept - 24 Sept
A Home Where Eclectic Luxury Meets Affordability

4. 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.
The price is AU$475
includes taxes & fees
21 Sept - 22 Sept
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.

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, (22 reviews)
"Host responded quickly to our texts.Location was excellent for our needs."
United States
Angie Y.
The price is AU$258
includes taxes & fees
30 Sept - 1 Oct
Renovated Peaceful Luxury Walk to Mall Park Publix
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

6. 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, (57 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is AU$345
includes taxes & fees
30 Sept - 1 Oct
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

7. 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$243
includes taxes & fees
20 Sept - 21 Sept
Sunshine Escape Guesthouse ☀
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$451
includes taxes & fees
21 Sept - 22 Sept
Home Sweet Home
A modern kitchen with white cabinetry, a central island with bar stools, a built-in microwave, and a window with a view.

9. 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$452
includes taxes & fees
26 Sept - 27 Sept
Welcoming 2-bedroom house with AC in charming Sanford
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$508
includes taxes & fees
19 Sept - 20 Sept
Tranquil 3-bedroom house in Sanford with AC, WiFi

11. 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
10.0 out of 10, Exceptional, (7 reviews)
"Great place to stay. We plan on staying again."
United States
Nancee H.
The price is AU$189
includes taxes & fees
24 Sept - 25 Sept
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a dining area with a glass table and white chairs.

12. River City Retreat

River City Retreat
Sanford
9.6 out of 10, Exceptional, (21 reviews)
"Great place and quick, simple check in."
United States
Dennis L.
The price is AU$308
includes taxes & fees
23 Sept - 24 Sept
River City Retreat
A modern living room with a ceiling fan, a flat-screen TV, and a dining area with a white table and chairs.

13. 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, (4 reviews)
"The home is beautiful!! The place was clean, comfortable, and exactly as described. The host was friendly, responsive, and made everything easy. I would definitely stay here again and recommend it to others."
United States
Breasia J.
The price is AU$501
includes taxes & fees
27 Sept - 28 Sept
The Canopy on Periwinkle- A Home Away From Home
A covered porch with two blue chairs and a small table, wooden flooring, and a door with a 'Home Sweet Home' sign.

14. Historic Hotspot • Walk to Downtown Fun • Luxury Beds

Historic Hotspot • Walk to Downtown Fun • Luxury Beds
Downtown Sanford
10.0 out of 10, Exceptional, (19 reviews)
"Ideal location, easy walk to food and fun."
United States
Steven H.
The price is AU$314
includes taxes & fees
20 Sept - 21 Sept
Historic Hotspot • Walk to Downtown Fun • Luxury Beds
A gray front door with a glass panel, a wreath, and a doormat with the text "so happy you're here."

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, (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$253
includes taxes & fees
13 Oct - 14 Oct
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

16. 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$378
includes taxes & fees
13 Oct - 14 Oct
Spacious 5-bedroom house in gorgeous Winter Park
A bedroom with a bed, bedside table, lamp, TV, fireplace, and a window with curtains.

17. 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$552
includes taxes & fees
20 Sept - 21 Sept
Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10
A modern kitchen with wooden cabinets, a black countertop, a stainless steel refrigerator, a microwave, and a coffee maker.

18. Stylish & Cozy King Bed Retreat @ Baldwin Park

Stylish & Cozy King Bed Retreat @ Baldwin Park
Orlando
10.0 out of 10, Exceptional, (17 reviews)
"Highly recommend this property. Very clean, beautiful location, and so comfortable !"
United States
Luis G.
The price is AU$449
includes taxes & fees
21 Sept - 22 Sept
Stylish & Cozy King Bed Retreat @ Baldwin Park
A two-story yellow house with a porch, surrounded by lush greenery and trees.

19. 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$560
includes taxes & fees
18 Sept - 19 Sept
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
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, (9 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
21 Sept - 22 Sept
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 Longwood Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Everything was perfect"
Joshua 1-night trip
Posted less than an hour ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Find out more about Longwood

Longwood Holiday Homes information

Number of reviews
326
Accommodation
1671 Holiday Homes
Lowest Price
AU$189
Highest Price
AU$2,731