Longwood Cottages

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Longwood cottages

A single-story building with the number 297, a red door, and a bench outside.

1. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Lake Mary

Gary

includes taxes & fees

16 Nov - 17 Nov

A patio with outdoor furniture, a wooden deck, and a basketball hoop.

2. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Lake Mary

Chiann M.

includes taxes & fees

2 Dec - 3 Dec

A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

3. Downtown Cottage

Colonialtown North

Jerred B.

includes taxes & fees

3 Nov - 4 Nov

A white building with large windows and a brick pathway leading to it.

4. The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!

College Park

Raegan S.

includes taxes & fees

3 Nov - 4 Nov

A small house with a porch, a red door, and potted plants.

5. The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

Lake Helen

Stacy S.

includes taxes & fees

16 Nov - 17 Nov

A serene landscape with a pond, trees with Spanish moss, and a palm tree.

6. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Windermere

includes taxes & fees

16 Nov - 17 Nov

A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

7. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Orlando

includes taxes & fees

3 Nov - 4 Nov

A covered porch with wicker chairs and a ceiling fan.

8. Historic Tremain Cottages

Mount Dora

Charlotte

includes taxes & fees

3 Nov - 4 Nov

A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

9. Fire Pit & Yard: Updated Winter Garden Home!

Winter Garden

includes taxes & fees

3 Nov - 4 Nov

A small, single-story house with a gabled roof and a front porch.

10. Mount Dora Cottages

Mount Dora

PATRICIA

includes taxes & fees

3 Nov - 4 Nov

A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

11. Th60 - 3BR House Near Disney With Pool Access

Orlando

includes taxes & fees

9 Nov - 10 Nov

A well-lit garden area with a gravel pathway, decorative lights, and various plants.

12. Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Mount Dora

Thomas K.

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with a table and chairs, a white building with large windows, and a wooden fence.

13. Beautiful Historic Cottage, Nantucket

Mount Dora

University Sports M.

includes taxes & fees

3 Nov - 4 Nov

A covered porch with white wicker furniture and green cushions, large windows, and a ceiling fan.

14. Beautiful Historic Cottage, The Garden

Mount Dora

Mark

includes taxes & fees

3 Nov - 4 Nov

A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

15. Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Orlando

includes taxes & fees

3 Nov - 4 Nov

A hallway with a dining area, a black metal chair, and a sign reading "Rendezvous".

16. Beautiful Historic Cottage, Rendezvous

Mount Dora

Julie

includes taxes & fees

3 Nov - 4 Nov

17. Th20 - 3BR House With Resort Access Near Parks

Orlando

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Longwood Hotel Reviews

DoubleTree by Hilton Orlando Theme Park Resort

8/10 Good

"none"

Four Points by Sheraton Orlando International Drive

8/10 Good

"The hotel itself is in a convenient location. The staff was nice and the lobby smelled really good. However, the rooms were pretty run down. And also, they say they have transportation to the parks. But it isn’t like the other hotels in the area that come and go all the time. They have a few drop off and pick up times and that’s it. They also only do room service every other day so since we only stayed two nights we never had service."

Find out more about Longwood