Legacy Trail Holiday Rentals

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Our top choices for Legacy Trail holiday rentals

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.6 out of 10, Exceptional, (95 reviews)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is AU$869
includes taxes & fees
6 Apr - 7 Apr
SeaSpray Resort

Condo in South Village

Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1,209 reviews)
"Staff really were accommodating. The location was perfect and the rooms were clean and quiet. We enjoyed the pool and beach."
United States
Glenn
The price is AU$480
includes taxes & fees
1 Apr - 2 Apr
Captiva Beach Resort

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5,343 reviews)
"Wonderful stay!"
United States
Victoria
The price is AU$459
includes taxes & fees
10 Mar - 11 Mar
Tropical Beach Resorts

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (258 reviews)
"Great place! "
United States
Michelle
The price is AU$264
includes taxes & fees
2 Apr - 3 Apr
Kon Tiki Inn

Holiday Home in Siesta Key

Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (60 reviews)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
The price is AU$856
includes taxes & fees
14 Mar - 15 Mar
Siesta Key Island Rentals

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (600 reviews)
"The location is ideal, rooms are nice and the owners are extremely accommodating. "
United States
Catherine
A Beach Retreat
3.0 star property
8.8 out of 10, Excellent, (5 reviews)
"A bargain given the cost of other hotels. Nice being hosted by Christians!"
United States
Patrick
The price is AU$184
includes taxes & fees
29 Mar - 30 Mar
Christian Retreat Conference Center

Apartment in Bradenton Beach

Pelican Post at Anna Maria Island Inn
3.5 star property
9.2 out of 10, Wonderful, (372 reviews)
"Room was clean and great location."
United States
Jennifer
Pelican Post at Anna Maria Island Inn

Apartment in Siesta Key

The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (354 reviews)
"great location, very clean, quiet"
United States
Joaquin
The Ringling Beach House

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (194 reviews)
"Great place to stay! "
United States
Carlos
The price is AU$910
includes taxes & fees
9 Mar - 10 Mar
The Inn On Siesta Key

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (16 reviews)
"Great place and location "
United States
Cathy
The price is AU$1,067
includes taxes & fees
20 Mar - 21 Mar
Chadwick Cove Resort & Marina
2.5 star property
8.6 out of 10, Excellent, (2,265 reviews)
"Very clean, and staff was extremely nice. "
United States
Maribeth
The price is AU$404
includes taxes & fees
5 Apr - 6 Apr
Hibiscus Suites - Gateway to Siesta Key
9.4 out of 10, Exceptional, (112 reviews)
"Great location for a quick beach getaway!"
United States
Thomas D.
The price is AU$818
includes taxes & fees
14 Mar - 15 Mar
Casey Key Beachfront Escape: Charming 1BR Cottage
9.2 out of 10, Wonderful, (179 reviews)
"Wonderful property with an excellent location! Beach access was across the street and the trolley pick-up was at the end of the block. The village was within walking distance as well. The property was very clean and the beds were comfortable. The washer and dryer is located right outside of the unit and beach chairs and a cooler were provided. We look forward to booking this property again in the future! "
United States
Alison B.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
10.0 out of 10, Exceptional, (22 reviews)
"During the week the stay was perfect. We were steps from the beach. The property abuts to the public park which meant dramatically increased crowds on the weekend. Very nice stay."
United States
Diana M.
The price is AU$1,068
includes taxes & fees
8 Mar - 9 Mar
Mello on the Beach - Shore Enuff
9.2 out of 10, Wonderful, (133 reviews)
"Location was great! Can walk to shopping and restaraunts. Host was great with communication. Great stay!"
United States
Kristi R.
The price is AU$1,712
includes taxes & fees
23 Mar - 24 Mar
House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

Condo in Holmes Beach

Mello on the Beach - Sol Mate
9.8 out of 10, Exceptional, (31 reviews)
"Mello was beautiful, close to the beach very welcoming and had all that you may need."
United States
Brendan N.
The price is AU$1,065
includes taxes & fees
8 Mar - 9 Mar
Mello on the Beach - Sol Mate

Holiday Home in Olde Englewood Village

Old Floridian cottage in Historic Gulf Village
9.8 out of 10, Exceptional, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is AU$474
includes taxes & fees
1 Apr - 2 Apr
Old Floridian cottage in Historic Gulf Village
9.6 out of 10, Exceptional, (61 reviews)
"We just needed to get away. This was the prefect spot. We would definitely come back. The view of the water was amazing "
United States
Angela S.
The price is AU$699
includes taxes & fees
8 Mar - 9 Mar
3 Bedroom-Beachfront Condo with Most Amazing Sunset Views of the Gulf

Apartment in Holmes Beach

Palm Tree Villas
3.0 star property
9.2 out of 10, Wonderful, (173 reviews)
"We had a great stay! The property was located within a short walk to the beach. We will be back!"
United States
Anonymous traveller
Palm Tree Villas
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.

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Top Legacy Trail Hotel Reviews

Find out more about Legacy Trail

Everything you need to know about Legacy Trail holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Legacy Trail holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Legacy Trail holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Legacy Trail holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Legacy Trail. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Legacy Trail holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Legacy Trail holiday rentals we have selected for you start as low as AU$250 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Legacy Trail rentals

At Expedia, we put the best Legacy Trail holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Legacy Trail rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Legacy Trail holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Legacy Trail. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.