Compare Legacy Trail Cottage Rentals

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

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
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.
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
The "Grouper"

The "Grouper"

This cottage is a smoke-free cottage.
Kitchen
Pet friendly
1 Bedroom Duplex On Intracoastal W/ Beach Access

1 Bedroom Duplex On Intracoastal W/ Beach Access

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Country Cottage Home

Country Cottage Home

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Washer
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

At this cottage, guests have access to laundry facilities, local meal delivery service, and a garden.
Kitchen
Washer
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

Guests of this cottage enjoy free WiFi in public areas, a library, and local meal delivery service. Additional amenities include barbecue grills and a garden.
Pool
Kitchen
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

Guests staying at this cottage enjoy a gym, laundry facilities, and local meal delivery service. Other amenities at this beach cottage include a garden and barbecue grills.
Kitchen
Washer
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

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

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Legacy Trail
View all properties
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

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
58 Cottages
Lowest Price
Highest Price
Popular accommodation
The Inn On Siesta Key, Charming cottage in quiet area, close to beach & bay. , The "Grouper", 1 Bedroom Duplex On Intracoastal W/ Beach Access, Country Cottage Home, Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi, This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL., Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill, Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Cottages in Legacy Trail

Most Popular

More Places To Stay in Legacy Trail

Book on Expedia