Legacy Trail Beach Vacations

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Top Beach vacation packages in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,305, price is now $765 per person
$765
per person
Jan 5 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,803 reviews)
Clean room, convenient, and beautiful Christmas decor!

Reviewed on Dec 2, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was $2,683, price is now $1,369 per person
$1,369
per person
Feb 19 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Room was great. Reception awesome. Location awesome. However, the washer stopped working middle of night - resulting in our laundry being stuck (door locked, would not release as water error). We couldn't get fixed. By time maintenance got fixed, we had to check out. TO credit, they mailed our laundry to us, but we needed it the for the next 3 days of our vacaction, and didn't have it available.

Reviewed on Nov 26, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $3,268, price is now $1,777 per person
$1,777
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (712 reviews)
Excellent, Excellent, Excellent. From the staff, the way the room looked. Everything is included in the room that you would need for your stay. Can't wait to visit again.

Reviewed on Dec 2, 2025

Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
Save 100% on your flight
Price was $1,383, price is now $798 per person
$798
per person
Feb 14 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.4/10 Exceptional! (1,843 reviews)
Clean room good location, bathroom sink drained the water very slowly it was annoying

Reviewed on Dec 1, 2025

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Save 100% on your flight
Price was $1,774, price is now $1,045 per person
$1,045
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
7/10 Good! (1,744 reviews)
Great location, nice view.

Reviewed on Dec 2, 2025

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5* Beach vacations in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
The Adaline

The Adaline

5 out of 5
Hyde Park
Save 100% on your flight
Price was $1,574, price is now $1,119 per person
$1,119
per person
Feb 18 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
9.6/10 Exceptional! (53 reviews)
Very cute place! Feels like home. It’s in a walkable area really close to a lot of stores and food options. I enjoyed staying here!

Reviewed on Dec 1, 2025

The Gemma by Brightwild

The Gemma by Brightwild

5 out of 5
Save 100% on your flight
Price was $8,232, price is now $4,866 per person
$4,866
per person
Feb 19 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
10/10 Exceptional! (2 reviews)
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

5 out of 5
Central Sarasota
Save 100% on your flight
Price was $3,938, price is now $3,122 per person
$3,122
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
We stayed on the Club Level, and the concierges were great!!! They couldn't do enough for us! The front desk staff were great too! It was Halloween, and they celebrated in style!

Reviewed on Nov 6, 2025

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3 Night Beach vacations in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $851, price is now $512 per person
$512
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.4/10 Exceptional! (67 reviews)
The place was very nicely furnished and spotless. The bedrooms were spacious and the beds and bedding were extremely comfortable. The living room furniture was the best I’ve seen in a rental. They had beach bags, chairs, wagons, and quality beach towels at our disposal. The unit is only a half of a block to the beach and a half of a mile to The Village with restaurants and bars.

Reviewed on Dec 2, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,993, price is now $1,151 per person
$1,151
per person
Feb 13 - Feb 16
found 2 days ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Room was great. Reception awesome. Location awesome. However, the washer stopped working middle of night - resulting in our laundry being stuck (door locked, would not release as water error). We couldn't get fixed. By time maintenance got fixed, we had to check out. TO credit, they mailed our laundry to us, but we needed it the for the next 3 days of our vacaction, and didn't have it available.

Reviewed on Nov 26, 2025

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Save 100% on your flight
Price was $860, price is now $515 per person
$515
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
New York (JFK) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (1,612 reviews)
Nice place to stay, but two previous restaurants are now closed.

Reviewed on Dec 1, 2025

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4 Night Beach vacations in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Palm River-Clair Mel
Save 100% on your flight
Price was $800, price is now $381 per person
$381
per person
Jan 9 - Jan 13
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
2/10 (2 reviews)
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Save 100% on your flight
Price was $1,115, price is now $580 per person
$580
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (1,612 reviews)
Nice place to stay, but two previous restaurants are now closed.

Reviewed on Dec 1, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
South Village
Price was $2,510, price is now $1,341 per person
$1,341
per person
Feb 11 - Feb 15
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.6/10 Exceptional! (294 reviews)
Suite 601 is an exceptional ocean front room with views of sunrise and sunset. The room has top notch appliances and was sparkling clean!

Reviewed on Nov 24, 2025

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Find your perfect Legacy Trail beach vacation

How do I book the best Legacy Trail beach vacation packages?

Life’s a beach when you dive into our brilliant Legacy Trail beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Legacy Trail?

A rental steps from the shore creates an amazingly affordable Legacy Trail beach vacation. Seaside sojourns during low season start from $381. Prices and availability are subject to change. Additional terms may apply.

When should I book a Legacy Trail beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Legacy Trail?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Legacy Trail beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Legacy Trail vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Legacy Trail beach vacation deals?

Sort your search results by deals to delight in amazing Legacy Trail beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Legacy Trail beach trip with free cancellation and/or flexible dates?

Just like the Legacy Trail tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Legacy Trail beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Legacy Trail. (OK, maybe not that last part.)

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.