Gillespie Park Vacations from $785

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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.
Resort Sixty-Six

Resort Sixty-Six

Save 100% on your flight
$785
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
9/10 Wonderful! (8 reviews)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
Save 100% on your flight
$869
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,128 reviews)
Everything was good

Reviewed on Aug 17, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

Save 100% on your flight
$1,428
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (568 reviews)
Staff was extremely friendly and helpful will definitely be returning

Reviewed on Aug 15, 2026

The Westin Sarasota

The Westin Sarasota

Central Sarasota
Save 100% on your flight
$924
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,151 reviews)
Perfect stay!

Reviewed on Aug 17, 2026

Captiva Beach Resort

Captiva Beach Resort

South Village
Save 100% on your flight
$948
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,294 reviews)
The proximity to the beach and the ambient of the place

Reviewed on Aug 17, 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.

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

2 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 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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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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Gillespie Park Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
$64 nightly
$72 total
Aug 23 - Aug 24
Total with taxes and fees
9.2/10 Wonderful! (5,863 reviews)
"Very friendly personnel"

Reviewed on Aug 17, 2026

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
$175 nightly
$198 total
Aug 24 - Aug 25
Total with taxes and fees
9.4/10 Exceptional! (2,477 reviews)
"Elissa was great at the check in"

Reviewed on Aug 17, 2026

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
$158 nightly
$179 total
Aug 18 - Aug 19
Total with taxes and fees
Tropical Beach Resorts
See all 14,986 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
98% 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

$131
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.