Compare Live Oak Island Guest House Rentals

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Featured Guest Houses in Live Oak Island

The Heirloom Inn

The Heirloom Inn

3 out of 5
644 N Donnelly St Mount Dora FL
$178 nightly
The price is $192 total per night
$192 total
Jan 1 - Jan 2, 2026
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
$146 nightly
The price is $164 total per night
$164 total
Dec 17 - Dec 18
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 Estate at Mount Dora

The Estate at Mount Dora

3.5 out of 5
1029 E 5th Avenue Mount Dora FL
$123 nightly
The price is $137 total per night
$137 total
Dec 17 - Dec 18
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 Ann Stevens House

The Ann Stevens House

3 out of 5
201 E Kicklighter Rd Lake Helen FL
$159 nightly
The price is $179 total per night
$179 total
Dec 17 - Dec 18
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
SPRING LAKE GETAWAY SUITE (Detached Guest House)

SPRING LAKE GETAWAY SUITE (Detached Guest House)

Altamonte Springs FL
At this guesthouse, guests enjoy features like beach towels.
Free WiFi
Air conditioning
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

Sorrento FL
At this guesthouse, guests have access to features like laundry facilities. This guesthouse also has barbecue grills.
Pet friendly
Free WiFi
City Guesthouse in beautiful Historic Downtown Sanford

City Guesthouse in beautiful Historic Downtown Sanford

Sanford FL
This guesthouse is a smoke-free guesthouse.
Air conditioning
Parking available
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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 Live Oak Island

    Hilton Orlando/Altamonte Springs

    Hilton Orlando/Altamonte Springs

    350 S Northlake Blvd Altamonte Springs FL
    $126 nightly
    The price is $143 total per night from Dec 21 to Dec 22
    $143 total
    Dec 21 - Dec 22
    Total with taxes and fees
    8.8/10 Excellent! (1,193 reviews)
    La Quinta Inn & Suites by Wyndham Orlando Lake Mary

    La Quinta Inn & Suites by Wyndham Orlando Lake Mary

    1060 Greenwood Blvd Lake Mary FL
    $89 nightly
    The price is $102 total per night from Dec 17 to Dec 18
    $102 total
    Dec 17 - Dec 18
    Total with taxes and fees
    8.4/10 Very Good! (1,960 reviews)
    Hilton Garden Inn Apopka City Center

    Hilton Garden Inn Apopka City Center

    580 E. Main Street Apopka FL
    $103 nightly
    The price is $116 total per night from Dec 29 to Dec 30
    $116 total
    Dec 29 - Dec 30
    Total with taxes and fees
    9.2/10 Wonderful! (937 reviews)

Live Oak Island Guest Houses essential information

Accommodation
7 Guest Houses
Lowest Price
$102
Highest Price
$192
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),  Peaceful Two Bedroom Guest House near Wekiva River and State Parks , City Guesthouse in beautiful Historic Downtown Sanford

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