Compare Live Oak Island Cottage Rentals

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Featured Cottages in Live Oak Island

Tiny Hidden Cottage

Tiny Hidden Cottage

Longwood FL
$131 nightly
The price is $144 total per night
$144 total
Dec 21 - Dec 22
Total with taxes and fees
Guests staying at this cottage enjoy features like a water park.
Kitchen
Free WiFi
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

Lake Helen FL
At this cottage, guests have access to barbecue grills.
Kitchen
Air conditioning
Historic Tremain Cottages

Historic Tremain Cottages

3 out of 5
619 N Tremain St Mount Dora FL
$177 nightly
The price is $197 total per night
$197 total
Dec 25 - Dec 26
Total with taxes and fees
Historic Tremain Cottages features free WiFi in public areas and barbecue grills. If you drive, take advantage of free parking.
Kitchen
Pet friendly
Cozy Mount Dora Cottage /Walk Downtown/ Pet Friendly / Fenced Yard

Cozy Mount Dora Cottage /Walk Downtown/ Pet Friendly / Fenced Yard

Mount Dora FL
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Washer
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood

High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood

Mt Dora FL
Guests staying at this cottage have access to local meal delivery service, a garden, and barbecue grills.
Kitchen
Free WiFi
Family Time! This Cute Cottage is waiting you for a unique experience!

Family Time! This Cute Cottage is waiting you for a unique experience!

Umatilla FL
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Guesthouse Retreat – Private Pool & King Suite

Guesthouse Retreat – Private Pool & King Suite

Lake Mary FL
$246 nightly
The price is $273 total per night
$273 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This cottage features an outdoor pool and laundry facilities.
Pool
Kitchen
Birds & Buns Bungalow

Birds & Buns Bungalow

De Leon Springs FL
$130 nightly
The price is $144 total per night
$144 total
Dec 17 - Dec 18
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, a living plant wall, and a garden. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Mount Dora FL
$257 nightly
The price is $282 total per night
$282 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
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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
    $120 nightly
    The price is $136 total per night from Dec 22 to Dec 23
    $136 total
    Dec 22 - Dec 23
    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)

Cottages

Book a cottage in Live Oak Island
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Live Oak Island. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Live Oak Island better.

Cottage apartments in Live Oak Island range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Live Oak Island
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Live Oak Island and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Live Oak Island cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Live Oak Island. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Live Oak Island Cottages essential information

Accommodation
97 Cottages
Lowest Price
$102
Highest Price
$282
Popular accommodation
Tiny Hidden Cottage , The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland. , Historic Tremain Cottages, Cozy Mount Dora Cottage /Walk Downtown/ Pet Friendly / Fenced Yard, High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood, Family Time! This Cute Cottage is waiting you for a unique experience!, Guesthouse Retreat – Private Pool & King Suite, Birds & Buns Bungalow, Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

More to Explore