Gillespie Park Vacations from $818

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Your Gillespie Park Vacation

Organizing your next travel adventure just got easier with a vacation package to Gillespie Park. Experience the very best this neighborhood has to offer while creating precious memories you'll remember for years. Your trip to Gillespie Park wouldn't be complete without a visit to top attractions nearby such as St. Armands Circle, Mote Marine Laboratory & Aquarium and Marie Selby Botanical Gardens. No matter your travel goals or budget, booking your dream Gillespie Park vacation is easy with Expedia.

The Latest Gillespie Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
Save 100% on your flight
$818
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,236 reviews)
Okay hotel but nowhere near the price premium that was paid, not sure how this hotel has such high reviews this was our most expensive reservation and left the most to be desired. Not a bad spot, but definitely not outstanding.

Reviewed on Oct 1, 2026

CW Resort

CW Resort

Save 100% on your flight
$870
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (188 reviews)
Dilan was an amazing help on our first night throughly explaining all questions asked. We went on the dolphin jet ski adventure through the resort. It was super fun and we definitely saw some dolphins. Stephanie was our leader and she was very personable and nice as well as dilan. Drinks and food are great as well. Our room was super clean and had amazing views of the ocean.

Reviewed on Oct 1, 2026

Stylish Treasure Island Escape

Stylish Treasure Island Escape

Sunshine Beach
Save 100% on your flight
$4,987
per person
Dec 22 - Dec 28
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
No reviews
The Avalon Club

The Avalon Club

Save 100% on your flight
$1,093
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (605 reviews)
The place was so clean and put together. I would recommend this place to anyone.

Reviewed on Oct 1, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

$1,828
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (603 reviews)
Best place to stay on island!

Reviewed on Oct 1, 2026

Where to stay in Gillespie Park

Find the best Gillespie Park areas and neighborhoods for the activities you enjoy most. Learn more about Gillespie Park
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.

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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.

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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.

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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 Turtle Beach, some noteworthy sights in the nearby area.

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Gillespie Park Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (6,074 reviews)
"Clean room, helpful staff, beautiful property"

Reviewed on Oct 1, 2026

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Kompose Boutique Hotel
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (2,594 reviews)
"Everything was fantastic!"

Reviewed on Oct 1, 2026

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Compass Hotel by Margaritaville Anna Maria Sound
Tropical Beach Resorts

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
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Tropical Beach Resorts
See all 15,249 properties in Gillespie Park
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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Stay near popular Gillespie Park attractions

Sarasota County Visitor Information Center

8.0/10 (4 reviews)
Sarasota County Visitor Information Center is just one of the places to see in Sarasota, so why not enjoy the other things to explore during your travels? Stroll along the beautiful beaches or attend a sporting event in the area.
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Sarasota Childrens Garden

Enjoy the beautiful sunsets and explore Sarasota Childrens Garden, a lovely green space in Sarasota. Experience the area's fascinating museums or attend a sporting event.
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Things to do

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
Mangroves, Manatees & a Hidden Beach Kayak Tour

Mangrove Tunnel & Manatee Kayak Eco-Tour

$59
per adult
94% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
HydroCats - 2 Hour CraigCat Sightseeing Tour

HydroCats - 2 Hour CraigCat Sightseeing Tour

$146
per adult
100% of travellers recommend
HydroCats - 2 Hour CraigCat Sightseeing 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.