Book Guest Houses in Longwood, FL

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Guest Houses in Longwood

The Estate at Mount Dora

The Estate at Mount Dora

3.5 out of 5
1029 E 5th Avenue Mount Dora FL
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $131 total per night
$131 total
Apr 27 - Apr 28
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A terrace, a garden, and express check-in are also on offer.
Pet friendly
Parking included
The Heirloom Inn

The Heirloom Inn

3 out of 5
644 N Donnelly St Mount Dora FL
$137 nightly
The price is $145 total per night
$145 total
May 10 - May 11
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, express check-in, and express check-out are also on offer.
Pet friendly
Parking included
SPRING LAKE GETAWAY SUITE (Detached Guest House)

SPRING LAKE GETAWAY SUITE (Detached Guest House)

Altamonte Springs FL
Get rates
Stay at this guesthouse in Altamonte Springs. Enjoy free WiFi, balconies, and cable/satellite TV service. Our guests praise the helpful staff in our reviews. Popular attractions Wekiwa Springs State Park and Cranes Roost Park are located nearby.
Free WiFi
Air conditioning
Cabin On The Lake

Cabin On The Lake

3 out of 5
222 Tangerine Ave Lake Helen FL
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $165 total per night
$165 total
Apr 27 - Apr 28
Total with taxes and fees
This guesthouse features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Breakfast included
Spa
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$285 nightly
The price is $316 total per night
$316 total
May 4 - May 5
Total with taxes and fees
This guesthouse features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Winter Park Getaway

Winter Park Getaway

Winter Park FL
Get rates
This guesthouse includes a garden and barbecue grills.
Free WiFi
Air conditioning
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$328 nightly
The price is $365 total per night
$365 total
May 24 - May 25
Total with taxes and fees
This guesthouse features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and conveniences like a garden and barbecue grills.
Pool
Hot Tub
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$170 nightly
The price is $188 total per night
$188 total
Apr 28 - Apr 29
Total with taxes and fees
Stay at this guesthouse in Orlando. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Kia Center and Camping World Stadium are located nearby.
Free WiFi
Air conditioning
The Ann Stevens House

The Ann Stevens House

3 out of 5
201 E Kicklighter Rd Lake Helen FL
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $179 total per night
$179 total
Apr 30 - May 1
Total with taxes and fees
A bar/lounge and a terrace are featured at this guesthouse, along with free self parking. WiFi in public areas is free. A garden and express check-out are also provided.
Parking included
Free WiFi
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

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

Orlando FL
Get rates
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. A library is also provided.
Pool
Free WiFi
Sunrise to Sunset on private 900 sq ft dock with BBQ!

Sunrise to Sunset on private 900 sq ft dock with BBQ!

Tavares FL
Get rates
This guesthouse features a garden, laundry facilities, and barbecue grills.
Pet friendly
Free WiFi
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

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

Orlando FL
Get rates
A garden is available at this guesthouse.
Free WiFi
Air conditioning
Don't see what you're looking for?
See all available properties in Longwood
View all properties
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.

Top hotels in Longwood

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL
$133 nightly
The price is $150 total per night from May 25 to May 26
$150 total
May 25 - May 26
Total with taxes and fees
9/10 Wonderful! (6,659 reviews)

Longwood Guest Houses essential information

Accommodation
27 Guest Houses
Lowest Price
$77
Highest Price
$365
Popular accommodation
The Estate at Mount Dora, The Heirloom Inn, SPRING LAKE GETAWAY SUITE (Detached Guest House), Cabin On The Lake, Historic lakefront guesthouse, Winter Park Getaway, Mills Cottage by the Little Lake, Downtown Lake Eola Historic House 1 OR 2 BED, The Ann Stevens House, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, Sunrise to Sunset on private 900 sq ft dock with BBQ! , 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

Explore More Ways to Travel with Travelocity