Compare Legacy Trail Cottage Rentals

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Featured Legacy Trail Cottages

The "Grouper"

The "Grouper"

$190 nightly
The price is $212 total per night
$212 total
Oct 26 - Oct 27
Total with taxes and fees
This cottage is a smoke-free cottage.
Kitchen
Pet friendly
The Inn On Siesta Key

The Inn On Siesta Key

3.5 out of 5
515 Beach Road, Siesta Key, FL
Guests of The Inn On Siesta Key enjoy features like an outdoor pool, free WiFi in public areas, and free use of bicycles. If you decide to drive, there's free parking. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this beach cottage include a terrace, laundry facilities, and a garden.
Pool
Kitchen
Charming cottage in quiet area, close to beach & bay.

Charming cottage in quiet area, close to beach & bay.

Guests of this cottage enjoy access to a water park, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Country Cottage Home

Country Cottage Home

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Anna Maria Cottage with Golf Cart

Anna Maria Cottage with Golf Cart

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

$407 nightly
The price is $454 total per night
$454 total
Oct 21 - Oct 22
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Tropical Paradise On The Beach Permit VRC17-000168

Tropical Paradise On The Beach Permit VRC17-000168

At this cottage, guests have access to features like laundry facilities. This beach cottage also has barbecue grills.
Kitchen
Washer
Tropical Paradise Cottage on the Beach VRC17-000167

Tropical Paradise Cottage on the Beach VRC17-000167

At this cottage, guests have access to features like laundry facilities. This beach cottage also has barbecue grills.
Kitchen
Washer
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Pool
Kitchen
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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 Legacy Trail

    Kompose Boutique Hotel

    Kompose Boutique Hotel

    965 University Pkwy, Sarasota, FL
    $72 nightly
    The price is $82 total per night from Oct 21 to Oct 22
    $82 total
    Oct 21 - Oct 22
    Total with taxes and fees
    9/10 Wonderful! (4,508 reviews)
    Tropical Beach Resorts

    Tropical Beach Resorts

    6717 Sara Sea Circle, Siesta Key, FL
    $147 nightly
    The price is $166 total per night from Oct 21 to Oct 22
    $166 total
    Oct 21 - Oct 22
    Total with taxes and fees
    9.2/10 Wonderful! (5,043 reviews)
    Spark by Hilton Sarasota Siesta Key Gateway

    Spark by Hilton Sarasota Siesta Key Gateway

    6600 S Tamiami Trl, Sarasota, FL
    $114 nightly
    The price is $129 total per night from Oct 26 to Oct 27
    $129 total
    Oct 26 - Oct 27
    Total with taxes and fees
    8.2/10 Very Good! (1,774 reviews)

Cottages

Book a cottage in Legacy Trail
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Legacy Trail. 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 Legacy Trail better.

Cottage apartments in Legacy Trail 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 Legacy Trail
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 Legacy Trail 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 Legacy Trail 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 Legacy Trail. 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.

Legacy Trail Cottages essential information

Accommodation
51 Cottages
Lowest Price
$82
Highest Price
$454
Popular accommodation
The "Grouper", The Inn On Siesta Key, Charming cottage in quiet area, close to beach & bay. , Country Cottage Home, Anna Maria Cottage with Golf Cart, Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom, Tropical Paradise On The Beach Permit VRC17-000168, Tropical Paradise Cottage on the Beach VRC17-000167, Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

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