Compare Legacy Trail Cottage Rentals

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Featured Legacy Trail Cottages

The Inn On Siesta Key

The Inn On Siesta Key

3.5 out of 5
515 Beach Road, Siesta Key, FL
The price is $311 per night
$311
includes taxes & fees
$275 per night
May 8 - May 9
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. 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 beach cottage include a terrace, laundry facilities, and a garden.
The "Grouper"

The "Grouper"

The price is $211 per night
$211
includes taxes & fees
$189 per night
May 5 - May 6
This cottage is a smoke-free cottage.
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

The price is $599 per night
$599
includes taxes & fees
$537 per night
May 5 - May 6
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

The price is $555 per night
$555
includes taxes & fees
$497 per night
May 11 - May 12
At this cottage, guests have access to features like laundry facilities.
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 a garden.
Pool
Kitchen
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

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

The price is $575 per night
$575
includes taxes & fees
$515 per night
May 5 - May 6
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
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
ONLY 2 WKS LEFT IN MAY 5 Min walk to Beach & Village, Private Pool,On the Canal

ONLY 2 WKS LEFT IN MAY 5 Min walk to Beach & Village, Private Pool,On the Canal

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Across The Street From #1 Beach

Across The Street From #1 Beach

At this cottage, guests have access to features like laundry facilities and local meal delivery service.
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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
    The price is $98 per night from May 11 to May 12
    $98
    includes taxes & fees
    $87 per night
    May 11 - May 12
    8.8/10 Excellent! (3,853 reviews)
    Golden Host Resort - Sarasota

    Golden Host Resort - Sarasota

    4675 N Tamiami Trl, Sarasota, FL
    The price is $101 per night from May 5 to May 6
    $101
    includes taxes & fees
    $90 per night
    May 5 - May 6
    8.2/10 Very Good! (1,901 reviews)
    Spark by Hilton Sarasota Siesta Key Gateway

    Spark by Hilton Sarasota Siesta Key Gateway

    6600 S Tamiami Trl, Sarasota, FL
    The price is $113 per night from May 20 to May 21
    $113
    includes taxes & fees
    $100 per night
    May 20 - May 21
    8.2/10 Very Good! (1,264 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
45 Cottages
Lowest Price
$98
Highest Price
$599
Popular accommodation
The Inn On Siesta Key, The "Grouper", Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms, Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village, Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach, Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom, Charming cottage in quiet area, close to beach & bay. , ONLY 2 WKS LEFT IN MAY 5 Min walk to Beach & Village, Private Pool,On the Canal, Across The Street From #1 Beach

Cottages in Legacy Trail

Most Popular

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