North Trail Vacations from $613

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Your North Trail Vacation

Our North Trail vacation packages are a speedy and practical way to organize and book your next retreat. Discover the true character of this unique neighborhood without the bother of having to plan everything yourself. Not sure what to do during your trip to North Trail? Nearby attractions such as Sarasota Jungle Gardens, University of South Florida Sarasota and John and Mable Ringling Museum of Art are excellent places to start. Stop dreaming and start doing. When it's time to book your vacation to North Trail, Expedia will help get you there.

The Latest North Trail Vacation Packages

Price found within the past 48 hours. Click for updated prices.
4BR Spacious Paradise

4BR Spacious Paradise

Siesta Key Village
Save 100% on your flight
$613
per person
Oct 27 - Nov 1
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
10/10 Exceptional! (1 review)
voco Sarasota by IHG

voco Sarasota by IHG

Central Sarasota
Save 100% on your flight
$804
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,004 reviews)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

Save 100% on your flight
$1,358
per person
Nov 29 - Dec 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,003 reviews)
Hyatt Regency Clearwater Beach Resort and Suites

Hyatt Regency Clearwater Beach Resort and Suites

Save 100% on your flight
$738
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,303 reviews)
The room is clean they clean the room every day the staff are very nice and respectful…. I recommend

Reviewed on Sep 12, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

Save 100% on your flight
$929
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (591 reviews)
Beautiful private beach. Room was nice. Amenities were great. Housekeeping could have been a little better.

Reviewed on Sep 11, 2026

Where to stay in North Trail

Find the best North Trail areas and neighborhoods for the activities you enjoy most. Learn more about North Trail
A sandy beach path with people walking, a wooden fence, and a clear blue sky with clouds.

Lido Key

Traverse a winding woodland path and spend the afternoon on this island’s secluded beaches before ending at a beachside bar to enjoy a spectacular sunset.

Find hotels in Lido Key
A cityscape with a mix of modern and historic buildings, palm trees, and a cloudy sky.

South Sarasota

Though South Sarasota might not have many top sights, you can venture to the surrounding area to see attractions like Siesta Key Beach and The Landings.

Find hotels in South Sarasota
A waterfront with palm trees, a dock, and a clear blue sky.

Central Sarasota

1 out of top 10 points of interest in this area

Beaches, exotic gardens and a museum for a famous circus are located in the city’s central sector. Visit an upscale shopping area on an island of its own.

Find hotels in Central Sarasota
A wooden pier extending into a body of water with a cloudy sky above.

Downtown Sarasota

If you're spending some time in Downtown Sarasota, Sarasota Opera House and Regal Hollywood - Sarasota are top sights worth seeing.

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A beach with clear water, rocks, and a sunset.

Palmer Ranch

When in Palmer Ranch, you can plan a visit to Stoneybrook Golf & Country Club and Sarasota Square, some noteworthy sights in the nearby area.

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North Trail Hotel Deals

The Westin Sarasota

The Westin Sarasota

100 Marina View Drive Sarasota FL
Fully refundableReserve now, pay when you stay
$166 nightly
$187 total
Sep 13 - Sep 14
Total with taxes and fees
The Westin Sarasota
Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

202 North Tamiami Trail Sarasota FL
Fully refundableReserve now, pay when you stay
$163 nightly
$185 total
Sep 20 - Sep 21
Total with taxes and fees
8.8/10 Excellent! (1,741 reviews)
"I enjoyed my stay here. I totally recommend it."

Reviewed on Sep 11, 2026

Embassy Suites by Hilton Sarasota, FL
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

1111 Ritz Carlton Dr Sarasota FL
Fully refundableReserve now, pay when you stay
$592 nightly
$669 total
Oct 12 - Oct 13
Total with taxes and fees
The Ritz-Carlton, Sarasota
See all 14,941 properties in North Trail
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.
All Inclusive Vacations
All Inclusive Vacations
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Kid Friendly Vacations
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Golf Vacations
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Romantic Vacations
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LGBTQ Friendly Vacations
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Where to go when
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Honeymoon Vacations
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Solo Vacations

Stay near popular North Trail attractions

A modern building with a purple facade and a white performance arts hall.

Van Wezel Performing Arts Hall

8.4/10 (109 reviews)
See a diverse range of exciting musical, dance and comedy shows at this architectural landmark inspired by the jagged shape of seashells.
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An ornate theater with red seats and a stage.

Asolo Theatre for the Performing Arts

8.8/10 (3 reviews)
Choose shows that match your interest from this venue’s extensive line-up and enjoy watching in a regal playhouse.
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Marietta Museum of Art and Whimsy

You can spend time exploring the galleries in Marietta Museum of Art and Whimsy during your travels in Sarasota. Attend a sporting event or discover the area's beautiful sunsets.
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Beatrice Friedman Symphony Center

You can get tickets for a performance at Beatrice Friedman Symphony Center during your stay in Sarasota. Stroll along the area's beautiful beaches or experience its fascinating museums.
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beach near Rosemary District

Why not spend a lazy afternoon at beach near Rosemary District during your trip to Sarasota? Discover the area's art scene, or seek out its biking trails.
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Art Center Sarasota

7.4/10 (3 reviews)
You can spend an afternoon studying the exhibits at Art Center Sarasota during your trip to Sarasota. Stroll along the beautiful beaches or discover the area's beautiful sunsets.
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McCurdy's Comedy Theatre

You can make plans for a show at McCurdy's Comedy Theatre during your stay in Sarasota. Stroll along the beautiful beaches or discover the area's beautiful sunsets.
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beach near Pioneer Park

Why not spend a lazy afternoon at beach near Pioneer Park during your trip to Sarasota? Stroll along the marina or seek out the biking trails.
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Things to do

Sarasota - Clear Kayak LED Night Glass Bottom Tour

Sarasota - Clear Kayak LED Night Glass Bottom Tour

$65
per adult
78% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
Picture 4 for Activity Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

$55
per adult
100% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
Taking in the views of another epic Siesta Key sunset!

Siesta Key Electric Bike Sunset Tour

$71
per adult
96% of travellers recommend
Siesta Key Electric Bike Sunset Tour
See all activities in Sarasota
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.