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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Longwood holiday homes

A hallway with a large wall clock, wicker baskets, a potted plant, and a door leading to a room with a chair and a small table.

1. The Longwood Escape • Modern Private Guesthouse Near Orlando

The Longwood Escape • Modern Private Guesthouse Near Orlando
Longwood
The price is NZ$281
includes taxes & fees
27 Oct - 28 Oct
The Longwood Escape • Modern Private Guesthouse Near Orlando
A playground with swings and a slide, surrounded by trees and a fenced area.

2. Longwood Pool Escape | Fire Pit & Sunny Patio

Longwood Pool Escape | Fire Pit & Sunny Patio
Longwood
The price is NZ$749
includes taxes & fees
27 Oct - 28 Oct
Longwood Pool Escape | Fire Pit & Sunny Patio
A two-story house with a driveway leading to a garage, surrounded by trees and a landscaped garden.

3. 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
8.4 out of 10, Very good, (5 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 NZ$3,009
includes taxes & fees
22 Oct - 23 Oct
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

4. 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)
"This home was just what we needed, it was clean and comfortable. Great communication with the owner. Nice, safe neighborhood."
United States
Angie P.
The price is NZ$418
includes taxes & fees
22 Oct - 23 Oct
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Private kitchen

5. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.2 out of 10, Wonderful, (49 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is NZ$591
includes taxes & fees
22 Oct - 23 Oct
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.

6. 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$332
includes taxes & fees
22 Oct - 23 Oct
Renovated Peaceful Luxury Walk to Mall Park Publix
A modern kitchen with white cabinets, a wooden dining table, and a hanging light fixture.

7. A Home Where Eclectic Luxury Meets Affordability

A Home Where Eclectic Luxury Meets Affordability
Altamonte Springs
9.8 out of 10, Exceptional, (129 reviews)
"The property was very well located and convenient to many restaurants. Lovely back yard."
United States
Sandra F.
The price is NZ$529
includes taxes & fees
29 Oct - 30 Oct
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.

8. 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$300
includes taxes & fees
25 Oct - 26 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.

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)
"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$569
includes taxes & fees
21 Nov - 22 Nov
Welcoming 2-bedroom house with AC in charming Sanford
Private kitchen

10. 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$233
includes taxes & fees
26 Oct - 27 Oct
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

11. Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (33 reviews)
"Everything was great! The host was extremely responsive and the area was extremely quiet. We will definitely stay here again on future vacations."
United States
Cameron A.
The price is NZ$543
includes taxes & fees
27 Oct - 28 Oct
Home Sweet Home
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

12. 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
26 Oct - 27 Oct
Tranquil 3-bedroom house in Sanford with AC, WiFi
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

13. 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$580
includes taxes & fees
1 Nov - 2 Nov
Spacious 5-bedroom house in gorgeous Winter Park
A modern kitchen with white cabinets, a stainless steel sink, and a dining area with a table and chairs.

14. 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$782
includes taxes & fees
23 Oct - 24 Oct
PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
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, (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 NZ$317
includes taxes & fees
3 Nov - 4 Nov
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
A modern living room with a sectional sofa, a coffee table, and a piano.

16. Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park Charmer - Heated Pool Home - Close to everything
Winter Park
8.4 out of 10, Very good, (21 reviews)
"Fabulous place with incredible value "
United States
Kyle C.
Winter Park Charmer - Heated Pool Home - Close to everything
A modern living room with a dining area, featuring a wooden floor, a gray sofa, a dining table with chairs, and a wall-mounted plant.

17. 2/1 with private backyard in the heart of Ivanhoe

2/1 with private backyard in the heart of Ivanhoe
Ivanhoe Village
8.0 out of 10, Very good, (16 reviews)
"Great location"
United States
Josh H.
The price is NZ$447
includes taxes & fees
22 Oct - 23 Oct
2/1 with private backyard in the heart of Ivanhoe
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$417
includes taxes & fees
17 Nov - 18 Nov
Modern Oasis in Orlando | Private Yard | Cabana
Terrace/patio

19. 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 NZ$273
includes taxes & fees
28 Oct - 29 Oct
Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
A modern bedroom with a yellow bed, a dark door, 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, (10 reviews)
"This cute lil place is perfect for a few nights for one person or a couple. It’s quiet, private and safe, and appointed with everything you need. The bed is comfy and the coffee was great. "
United States
Lindsay W.
The price is NZ$313
includes taxes & fees
26 Oct - 27 Oct
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

Grand Hotel Orlando at Universal Blvd - Shuttle to Theme Parks

Grand Hotel Orlando at Universal Blvd - Shuttle to Theme Parks

10/10 Excellent
"Una estadía excelente de principio a fin! Desde nuestra llegada, recibimos una atención amable y profesional por parte del personal. La habitación estaba limpia, cómoda y bien organizada, lo que nos permitió descansar y disfrutar de nuestra visita. Las instalaciones se encontraban en buenas condiciones y el ambiente fue agradable y tranquilo. Quiero destacar especialmente la hospitalidad del personal, siempre dispuesto a ayudar y hacer que los huéspedes se sientan bienvenidos. Sin duda, fue una experiencia muy positiva que superó nuestras expectativas. ¡Recomiendo este hotel y definitivamente volvería a hospedarme aquí en una próxima visita!"
WANDA 4-night trip
Posted less than an hour ago
Grand Hotel Orlando at Universal Blvd - Shuttle to Theme Parks

Find out more about Longwood

Longwood Holiday Homes information

Number of reviews
380
Accommodation
1664 Holiday Homes
Lowest Price
NZ$233
Highest Price
NZ$3,009