Photo by Kara Akers

Search Guest Houses in Longwood

  • Plan, book, stay with confidence

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

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 29 Guest Houses in Longwood with updated reviews, rates, and availability.

The Estate at Mount Dora

3.5 star property
9.2 out of 10, Wonderful, (352)
"Cute and nice place. Remembered me of my favorite book;) Bed was very comfortable. "
The price is AED 345
AED 481 total
includes taxes & fees
14 Apr - 15 Apr
The Estate at Mount Dora

The Heirloom Inn

3.0 star property
8.8 out of 10, Excellent, (203)
"We were staying for a weekend getaway, that included a proposal! We coyld not have had better accommodations. Very clean and comfortable. We will be staying every Anniversary now!"
The price is AED 367
AED 591 total
includes taxes & fees
1 May - 2 May
The Heirloom Inn

Cabin On The Lake

3.0 star property
9.8 out of 10, Exceptional, (92)
"Hugo was a wonderful host. He suggested various places to visit. He made great pancakes. It was fun watching him feed the ducks. Our room was clean and had everything we needed. The house was quiet and peaceful. It's worth a return trip. "
The price is AED 529
AED 595 total
includes taxes & fees
7 Apr - 8 Apr
Cabin On The Lake

The Ann Stevens House

3.0 star property
9.4 out of 10, Exceptional, (151)
"What a beautiful, serene, magical place this is! The owners are so friendly and helpful and full of so much knowledge about the area. We loved our stay and wanted to stay longer!! "
The price is AED 511
AED 574 total
includes taxes & fees
12 Apr - 13 Apr
The Ann Stevens House

Downtown Lake Eola Historic House 1 OR 2 BED

8.8 out of 10, Excellent, (29)
"We had an amazing time staying at this property. Everything was clean and the communication with the owner was amazing!"
The price is AED 312
AED 631 total
includes taxes & fees
7 Apr - 8 Apr
Downtown Lake Eola Historic House 1 OR 2 BED

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (64)
"Perfect house, perfect location, and the host is very pleasant and easy to get in contact with. A great stay."
SPRING LAKE GETAWAY SUITE (Detached Guest House)

Winter Park Getaway

10.0 out of 10, Exceptional, (3)
"The host was very helpful and welcoming without being overbearing as some can be. The space was clean, cute, and well stocked."
Winter Park Getaway

Cozy Tiny Cottage Farm House!

9.8 out of 10, Exceptional, (20)
"I needed a convenient place to stay while visiting family in Longwood, and this rental was perfect. Tucked away from the main road in a quiet neighborhood, the house was easy to find and check-in was effortless. The efficient space was well-appointed with all I needed for a cozy spot to sleep, have breakfast, and wash a small load of laundry before setting out to spend my day with family. I will be back."
Cozy Tiny Cottage Farm House!

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

10.0 out of 10, Exceptional, (79)
"The house was clean and pretty and perfect!! It’s all updated. Beds were super comfy and warm (it was cold the weekend we stayed). We did have an issue with a couple of minor things but Mike came over instantly and fixed them immediately. He was very attentive and very friendly and I enjoyed talking with him! We stayed for a soccer tournament and it was super close to Seminole Soccer Complex. I would absolutely stay there again! "
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

Mills Cottage by the Little Lake

10.0 out of 10, Exceptional, (44)
"Upon arriving nice neighborhood drive was seemed small but on our last day with multiple cars on lot it was easy to get out. I was impressed by the whole property, but the vegetation was by far my favorite thing the pool was easy to find there was so many things to keep us occupied if we needed. Owner was quick to respond and even checked in with us. Would definitely stay again!"
The price is AED 683
AED 1,416 total
includes taxes & fees
7 Apr - 8 Apr
Mills Cottage by the Little Lake

2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

9.2 out of 10, Wonderful, (15)
"This place was good for a two night pre cruise stay. Half of what you would pay staying at a hotel. A rental car is a must have for going anywhere. We just slept and showered here as we were out all day and brought takeout back. They provided a nice bottle of wine. I was disappointed that the bedding was not the nice white bedding pictured and was burgundy instead. A decent place to stay short term if you want to save on accommodations . "
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

Downtown Orlando Throne Historic Thornton Park

10.0 out of 10, Exceptional, (3)
"Property is in a great location of Thornton Park. We arrived and parked the car. Walking distance to everything, such an awesome weekend."
The price is AED 312
AED 838 total
includes taxes & fees
7 Apr - 8 Apr
Downtown Orlando Throne Historic Thornton Park

Beautiful Villa with Lake Views

10.0 out of 10, Exceptional, (2)
"UN APPARTEMENT TRES BIEN MEUBLÉ ET BIEN ÉQUIPÉ. UN AGRABLE SÉJOUR."
The price is AED 360
AED 933 total
includes taxes & fees
20 Apr - 21 Apr
Beautiful Villa with Lake Views

Cozy Guesthouse in Orlando, Florida! Convenience and comfort!

9.6 out of 10, Exceptional, (4)
"Very convenient location. New fixtures. Very clean. "
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (24)
"Samson and Sunny clearly put in the effort to make sure I felt welcome during my stay. The check in and check out processes were very simple (not always the case with properties!) which I really appreciated. "
Adorable 1bed 1 bath guest house

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

9.6 out of 10, Exceptional, (15)
"Walking distance to Vanguard."
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

City Guesthouse in beautiful Historic Downtown Sanford

9.8 out of 10, Exceptional, (8)
"The unit was nice though the AC was not operating properly. The Hosts were very understanding and immediately offer/processed refund and assisted in instructing us on method of cancelation to get full refund from VRBO. VRBO was also extremely prompt in processing a our full refund. This was a first for us using VRBO and was very skeptical but after this experience I will not have any reservation about using VRBO again as well as booking through this host. The AC issues were out of the hosts...
City Guesthouse in beautiful Historic Downtown Sanford

Private Poolside Guest House In Winter Park/Orlando

8.0 out of 10, Very Good, (2)
"The property, the location and host are all top notch."
Private Poolside Guest House In Winter Park/Orlando

Elegant Black & White 2BR | Pet-Friendly

2.0 star property
Elegant Black & White 2BR | Pet-Friendly

Blissful Guest House

3.0 star property
2.0 out of 10, (1)
Blissful Guest House
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.
Don't see what you're looking for?
See all available properties in Longwood
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Longwood

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (37)
"The cottage was cozy and complete, with even silverware and coffee cups. When the microwave stopped working, the owner went out and bought and set up a new microwave.She asked permission before showing up at the front door!"
The price is AED 290
AED 563 total
includes taxes & fees
7 Apr - 8 Apr
Tiny Hidden Cottage

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.2 out of 10, Wonderful, (1856)
"This hotel was conveniently attached to the Florida Mall and in a easy accessible location. It had ample parking and great location."
The price is AED 703
AED 886 total
includes taxes & fees
5 Apr - 6 Apr
Florida Hotel & Conference Center in the Florida Mall

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very Good, (997)
"Limited opcions for breakfast. We could not have eggs and pancakes at the same time, it was one are the other. Other than that, everything was ok."
The price is AED 308
AED 346 total
includes taxes & fees
9 Apr - 10 Apr
The View Studio Suites and Event Venue
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.