Longwood Vacation Homes

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

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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

Longwood

HK$1,316 total

includes taxes & fees

29 Sept - 30 Sept

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

Longwood

Tyler P.

HK$15,232 total

includes taxes & fees

2 Oct - 3 Oct

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

3. A Home Where Eclectic Luxury Meets Affordability

Altamonte Springs

"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."

Brenda N.

HK$2,404 total

includes taxes & fees

23 Sept - 24 Sept

A modern kitchen with a central island, white cabinets, a stainless steel refrigerator, and a black and white geometric backsplash.

4. Renovated Peaceful Luxury Walk to Mall Park Publix

Altamonte Springs

Angie Y.

HK$1,487 total

includes taxes & fees

29 Sept - 30 Sept

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

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

Casselberry

Kevin K.

HK$2,021 total

includes taxes & fees

26 Sept - 27 Sept

6. Florida Vacation with pool fun for families

Casselberry

Daniel W.

HK$2,647 total

includes taxes & fees

24 Sept - 25 Sept

A modern kitchen with wooden cabinets, a central island, and a built-in oven. There is a dining area with a blue sofa and a TV on the wall.

7. Charming Heated Pool home in Altamonte Springs

Altamonte Springs

Kyle T.

A modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

8. Sunshine Escape Guesthouse ☀

Orlando

Robin R.

HK$1,335 total

includes taxes & fees

23 Sept - 24 Sept

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

9. Home Sweet Home

Sanford

Janice M.

HK$2,513 total

includes taxes & fees

28 Sept - 29 Sept

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

Apopka

Nancee H.

HK$1,040 total

includes taxes & fees

24 Sept - 25 Sept

A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

11. CUTE and COZY studio w/ jacuzzi!

Azalea Park

Jackson K.

HK$1,401 total

includes taxes & fees

25 Sept - 26 Sept

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

Sanford

Rodney

HK$2,864 total

includes taxes & fees

24 Sept - 25 Sept

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

13. River City Retreat

Sanford

Dennis L.

HK$1,664 total

includes taxes & fees

28 Sept - 29 Sept

A modern living room with a ceiling fan, a flat-screen TV, and a dining area with a white table and chairs.

14. The Canopy on Periwinkle- A Home Away From Home

Goldenrod

Breasia J.

HK$2,832 total

includes taxes & fees

27 Sept - 28 Sept

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!

College Park

rimma

HK$1,304 total

includes taxes & fees

26 Sept - 27 Sept

A bedroom with a bed, nightstands, a desk, and a chair.

16. 1x1 Guest Suite 10 minutes from UCF

Union Park

Michael

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

Ivanhoe Village

Josh H.

HK$1,651 total

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a bed, bedside table, lamp, TV, fireplace, and a window with curtains.

18. Sanford's Sunset - Pet-friendly home, 4BR/sleeps 10

Sanford

Miriam R.

HK$3,157 total

includes taxes & fees

27 Sept - 28 Sept

A bedroom with a large bed, a desk with a chair, and a small table with a plant. There is a bathroom with a shower and a toilet visible through an open door.

19. Comfy studio in Central Orlando

Azalea Park

Diondra

HK$1,228 total

includes taxes & fees

23 Sept - 24 Sept

A modern kitchen with a central island, a dining area with a sofa and coffee table, and a large window providing a view.

20. Modern Oasis in Orlando | Private Yard | Cabana

Fairview Shores

Jason A.

HK$2,045 total

includes taxes & fees

19 Oct - 20 Oct

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Top Longwood Hotel Reviews

Ramada by Wyndham Suites Orlando Airport

10/10 Excellent

"Nothing"

Universal's Endless Summer Resort - Surfside Inn and Suites

8/10 Good

"this was a great budget resort for a trip to Universal. The rooms were clean, staff was friendly. We would have liked a restaurant or more food options on the premises but aside from that it was a great stay. Did get a little loud in the room when the room next door was a bit loud at night, we had an adjoining room so we could hear them through the adjoining door. Bus ride to the park was quick and easy. Overall we really enjoyed our stay."

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