Longwood Guest Houses
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Guest Houses in Longwood
The Heirloom Inn
644 N Donnelly St Mount Dora FL
$185 nightly
The price is $199 total per night
$199 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Located in Mount Dora, The Heirloom Inn is just steps from Donnelly Park and 7 minutes by foot from Lake Dora.
Pet friendly
Parking included
Cabin On The Lake
222 Tangerine Ave Lake Helen FL
$159 nightly
The price is $179 total per night
$179 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
Located in Lake Helen, Cabin On The Lake is in the historical district, within a 15-minute drive of Stetson University and Gemini Springs Park.
The Estate at Mount Dora
1029 E 5th Avenue Mount Dora FL
$128 nightly
The price is $142 total per night
$142 total
Dec 16 - Dec 17
Total with taxes and fees
Centrally located in Mount Dora, The Estate at Mount Dora is within a 15-minute walk of Mount Dora History Museum and Donnelly Park.
Pet friendly
Parking included
The Ann Stevens House
201 E Kicklighter Rd Lake Helen FL
$139 nightly
The price is $156 total per night
$156 total
Dec 12 - Dec 13
Total with taxes and fees
Located in Lake Helen, The Ann Stevens House is in a rural location, within a 15-minute drive of Stetson University and Blue Spring State Park.
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Altamonte Springs FL
Located in Altamonte Springs, this guesthouse is within a 15-minute drive of Kia Center and Camping World Stadium.
Downtown Lake Eola Historic House 1 OR 2 BED
Orlando FL
$129 nightly
The price is $142 total per night
$142 total
Dec 15 - Dec 16
Total with taxes and fees
With a stay at this guesthouse in Orlando (Downtown Orlando), you'll be within a 5-minute drive of Kia Center and Camping World Stadium.
Winter Park Getaway
Winter Park FL
Located in Winter Park, this guesthouse is within a 15-minute drive of Kia Center and University of Central Florida.
Mills Cottage by the Little Lake
Orlando FL
$289 nightly
The price is $321 total per night
$321 total
Dec 11 - Dec 12
Total with taxes and fees
With a stay at this guesthouse in Orlando (Lake Weldona), you'll be a 4-minute drive from Kia Center and 6 minutes from Camping World Stadium.
Historic lakefront guesthouse
Orlando FL
$240 nightly
The price is $266 total per night
$266 total
Dec 16 - Dec 17
Total with taxes and fees
When you stay at this guesthouse in Orlando, you'll be on a lake, within a 10-minute drive of Kia Center and Camping World Stadium.
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Orlando FL
With a stay at this guesthouse in Orlando, you'll be within a 5-minute drive of Universal Orlando Resort and The Wizarding World of Harry Potter™.
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.
Longwood Guest Houses essential information
Accommodation | 28 Guest Houses |
|---|---|
Lowest Price | $142 |
Highest Price | $321 |
Popular accommodation | The Heirloom Inn, Cabin On The Lake, The Estate at Mount Dora, The Ann Stevens House, SPRING LAKE GETAWAY SUITE (Detached Guest House), Downtown Lake Eola Historic House 1 OR 2 BED, Winter Park Getaway, Mills Cottage by the Little Lake, Historic lakefront guesthouse, 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio,  Peaceful Two Bedroom Guest House near Wekiva River and State Parks  |