Compare Longwood Guest House Rentals

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Featured 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
$128 nightly
The price is $142 total per night
$142 total
Oct 30 - Oct 31
Total with taxes and fees
A local mainstay since 1877, The Estate at Mount Dora offers free WiFi in public areas, express check-in, and express check-out. You can take advantage of free parking if you drive. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a terrace and a garden.
Pet friendly
Parking included
The Heirloom Inn

The Heirloom Inn

3 out of 5
644 N Donnelly St, Mount Dora, FL
$154 nightly
The price is $165 total per night
$165 total
Oct 26 - Oct 27
Total with taxes and fees
At The Heirloom Inn, guests have access to free WiFi in public areas, express check-in, and express check-out. Free parking is available if you drive. This guesthouse also has a garden.
Pet friendly
Parking included
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
$145 nightly
The price is $163 total per night
$163 total
Oct 27 - Oct 28
Total with taxes and fees
Guests of Cabin On The Lake enjoy a gym, free WiFi in public areas, and spa services. Free parking is included with your stay. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this golf guesthouse include coffee/tea in a common area, an arcade/game room, and barbecue grills.
Breakfast included
Spa
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
Oct 27 - Oct 28
Total with taxes and fees
A local mainstay since 1895, The Ann Stevens House offers free WiFi in public areas, express check-out, and a terrace. If you drive, take advantage of free parking. Friendly staff can provide tour or ticket assistance, and also offer advice about sightseeing. This guesthouse also has a garden.
Parking included
Free WiFi
Adorable 1bed 1 bath guest house

Adorable 1bed 1 bath guest house

Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Pet friendly
Free WiFi
Winter Park Getaway

Winter Park Getaway

Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

$310 nightly
The price is $344 total per night
$344 total
Oct 26 - Oct 27
Total with taxes and fees
Guests staying at this guesthouse enjoy an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly guesthouse include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

$155 nightly
The price is $172 total per night
$172 total
Oct 28 - Oct 29
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Air conditioning
Parking available
SPRING LAKE GETAWAY SUITE (Detached Guest House)

SPRING LAKE GETAWAY SUITE (Detached Guest House)

At this guesthouse, guests enjoy features like beach towels.
Free WiFi
Air conditioning
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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.

Hotel Options in Longwood

    Hyatt Regency Orlando International Airport

    Hyatt Regency Orlando International Airport

    9300 Jeff Fuqua Boulevard, Orlando, FL
    $169 nightly
    The price is $190 total per night from Oct 27 to Oct 28
    $190 total
    Oct 27 - Oct 28
    Total with taxes and fees
    9.4/10 Exceptional! (3,676 reviews)
    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 Nov 4 to Nov 5
    $150 total
    Nov 4 - Nov 5
    Total with taxes and fees
    8.8/10 Excellent! (5,442 reviews)
    DoubleTree by Hilton Hotel Orlando at SeaWorld

    DoubleTree by Hilton Hotel Orlando at SeaWorld

    10100 International Drive, Orlando, FL
    $101 nightly
    The price is $114 total per night from Nov 24 to Nov 25
    $114 total
    Nov 24 - Nov 25
    Total with taxes and fees
    7.4/10 Good! (6,172 reviews)

Longwood Guest Houses essential information

Accommodation
28 Guest Houses
Lowest Price
$114
Highest Price
$344
Popular accommodation
The Estate at Mount Dora, The Heirloom Inn, Cabin On The Lake, The Ann Stevens House, Adorable 1bed 1 bath guest house, Winter Park Getaway, Mills Cottage by the Little Lake, Downtown Lake Eola Historic House 1 OR 2 BED, SPRING LAKE GETAWAY SUITE (Detached Guest House)

More to Explore