Compare Legacy Trail Resorts

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Featured Resorts in Legacy Trail

Lido Beach Resort

Lido Beach Resort

4 out of 5
700 Benjamin Franklin Dr, Sarasota, FL
Free Cancellation
Reserve now, pay when you stay
$309 nightly
The price is $349 total per night
$349 total
Oct 22 - Oct 23
Total with taxes and fees
Guests of Lido Beach Resort have access to a private beach, 2 outdoor pools, and a gym. Valet parking is available for USD 20 per night. The front desk is staffed 24/7 to help with concierge services, dry cleaning/laundry, and securing valuables. 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 resort include free WiFi in public areas, a hot tub, and conference space.
On private beach
Pool
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 out of 5
5311 Ocean Blvd, Siesta Key, FL
$232 nightly
The price is $262 total per night
$262 total
Oct 21 - Oct 22
Total with taxes and fees
Guests staying at Siesta Key Beach Resort and Suites enjoy an outdoor pool, free WiFi in public areas, and a hot tub. Self parking is offered for USD 10 per day. Multilingual staff is on hand to answer questions. Additional amenities include free use of bicycles, express check-out, and a terrace.
Pool
Hot Tub
Zota Beach Resort

Zota Beach Resort

4 out of 5
4711 Gulf of Mexico Dr, Longboat Key, FL
Free Cancellation
Reserve now, pay when you stay
$249 nightly
The price is $281 total per night
$281 total
Oct 26 - Oct 27
Total with taxes and fees
Guests of Zota Beach Resort enjoy a private beach, an outdoor pool, and a gym. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, securing valuables, and concierge services. 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 resort include free WiFi in public areas, a hot tub, and meeting rooms.
On private beach
Pool
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
6900 Gulf Dr, Holmes Beach, FL
$342 nightly
The price is $387 total per night
$387 total
Nov 2 - Nov 3
Total with taxes and fees
Guests staying at Bali Hai Beachfront Resort and Spa enjoy access to a full-service spa, an outdoor pool, and free WiFi in public areas. You can take advantage of free parking if you drive. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this beach resort include coffee/tea in a common area, free use of bicycles, and laundry facilities.
Pool
Spa
The Resort at Longboat Key Club

The Resort at Longboat Key Club

4 out of 5
220 Sands Point Road, Longboat Key, FL
Free Cancellation
Reserve now, pay when you stay
$429 nightly
The price is $485 total per night
$485 total
Oct 26 - Oct 27
Total with taxes and fees
The Resort at Longboat Key Club features a private beach, a golf course, and a marina. There's free valet parking and an area shuttle. The 24-hour front desk has multilingual staff ready to assist with luggage storage, concierge services, and securing valuables. Other amenities at this beach resort include a full-service spa, an outdoor pool, and a 24-hour gym.
On private beach
Pool
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
2710 Gulf Drive N, Holmes Beach, FL
$312 nightly
The price is $353 total per night
$353 total
Oct 26 - Oct 27
Total with taxes and fees
At Cedar Cove Resort and Cottages, guests have access to free WiFi in public areas, coffee in a common area, and free use of bicycles. You can put free parking to good use if you drive. The front desk has multilingual staff that can help with luggage storage and concierge services. Other amenities at this beach resort include a terrace, laundry facilities, and a garden.
Parking included
Free WiFi
Newly updated in family/pet friendly resort with all the amenities - near beach!

Newly updated in family/pet friendly resort with all the amenities - near beach!

$204 nightly
The price is $227 total per night
$227 total
Oct 21 - Oct 22
Total with taxes and fees
Guests of this resort enjoy features like an outdoor pool, a gym, and laundry facilities. This smoke-free resort also has barbecue grills.
Pool
Pet friendly
Palm Bay Club Siesta Key Newley renovated !

Palm Bay Club Siesta Key Newley renovated !

Features of this resort include an outdoor pool and a gym.
Pool
Air conditioning
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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)

Resort Hotels

Resort hotels in Legacy Trail
Find your next great getaway when you book at a resort hotel in Legacy Trail. Resorts are great for families or couples, or even solo travelers looking for a piece of paradise. Sure, you can leave your hotel and explore Legacy Trail at your leisure…but with everything these sorts of hotels offer, you may never want to. From food and shopping to entertainment and organized tours, a resort hotel in Legacy Trail is a great way to score an amazing vacation—and Orbitz can help you get there.

Resort hotels for everyone in Legacy Trail
If you’re traveling with the kids, you know how hard it is to keep them entertained. Let them have some fun on their own: some resorts have clubs for the kiddos, including kid-friendly pools and adventure camps where they can explore, do some crafts and even take part in learning activities. (Don’t worry, no one will tell them this vacation is actually educational.) Of course, there’s plenty for adults to do at Legacy Trail resorts as well. Take a yoga class, book a few treatments at the spa, or do a little shopping. Go ahead, charge it to the room. You’re on vacation!

Ready to wow your special someone? Plan a romantic getaway complete with luxury accommodations. Surprise your partner with a couples massage, followed by a candlelit dinner at the 5-star on-site hotel. Some of these luxury hotels even have adults-only pools with swim-up bars so you can float about with a couple of cocktails, watching the sunset and enjoying your time together.

Legacy Trail Resorts essential information

Accommodation
8 Resorts
Lowest Price
$82
Highest Price
$485
Popular accommodation
Lido Beach Resort, Siesta Key Beach Resort and Suites, Zota Beach Resort, Bali Hai Beachfront Resort and Spa, The Resort at Longboat Key Club, Cedar Cove Resort and Cottages, Newly updated in family/pet friendly resort with all the amenities - near beach!, Palm Bay Club Siesta Key Newley renovated !

More to Explore