Compare Longwood Guest House Rentals
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Featured Guest Houses in Longwood

The Estate at Mount Dora
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
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
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
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
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Pet friendly
Free WiFi

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
$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
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
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
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
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) |
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