Gillespie Park Vacations from $359

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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.
SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Save 100% on your flight
Price was $607, price is now $359 per person
$359
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (417 reviews)
Great amenities, great staff

Reviewed on Jan 29, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,883, price is now $965 per person
$965
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Great staff perfect location for our stay.

Reviewed on Jan 27, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,359, price is now $779 per person
$779
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,097 reviews)
Amazing all around! Very impressed.

Reviewed on Jan 25, 2026

Lemon Bay Motel

Lemon Bay Motel

2 out of 5
Englewood Central
Save 100% on your flight
Price was $715, price is now $417 per person
$417
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
8.4/10 Very Good! (39 reviews)
Staff was great. Clean room but needs new rubber around the door.

Reviewed on Jan 29, 2026

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Save 100% on your flight
Price was $1,247, price is now $750 per person
$750
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
7/10 Good! (1,744 reviews)
The hotel was nice. The service in the restaurant was excellent. We loved having close access to the River Walk.

Reviewed on Jan 21, 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
Sarasota, Florida, USA Downtown Skyline

South Sarasota

While visiting South Sarasota, you might make a stop by sights like The Landings and Coconuts Family Entertainment Center.

Find hotels in South Sarasota

Gillespie Park Hotel Deals

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
4675 N Tamiami Trl Sarasota FL
Fully refundable
$88 nightly
The price is $99 total per night from Feb 1 to Feb 2
$99 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (2,244 reviews)
1950s Vintage Tiki Style Motel. Great staff, anything I needed they accosted immediately!

Reviewed on Jan 26, 2026

Golden Host Resort - Sarasota
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Feb 1 to Feb 2
$114 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (4,974 reviews)
Everything clean just obvious the it is a woke company

Reviewed on Jan 28, 2026

Kompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $233 total per night from Feb 1 to Feb 2
$233 total
Feb 1 - Feb 2
Total with taxes and fees
9.2/10 Wonderful! (5,261 reviews)
Nice

Reviewed on Jan 27, 2026

Tropical Beach Resorts
See all 14,653 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Gillespie Park

Lido Beach showing general coastal views and a sandy beach

Lido Beach

4.5/5(1,225 reviews)

Visit a beach not far from an upscale shopping area. The warm waters are as inviting as the white sand.

Lido Beach
St. Armands Circle featuring a statue or sculpture

St. Armands Circle

4.5/5(1,234 reviews)

Consider this area as a circular outdoor mall. Like any mall, you can shop, dine, browse or just people-watch. Unlike most malls, this one never closes to walkers.

St. Armands Circle
EJETFA The official entrance at the new Mall at University Town Center located just off I-75 on University Parkway in Sarasota Floria

Mall at University Town Center

4.5/5(363 reviews)

You can search for that perfect souvenir at Mall at University Town Center during your visit to Sarasota. Attend a sporting event or discover the beautiful sunsets in this family-friendly area.

Mall at University Town Center

Things to do

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

$59
per adult
92% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Sarasota - Clear Kayak LED Night Glass Bottom Tour

Sarasota - Clear Kayak LED Night Glass Bottom Tour

$65
per adult
80% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

$65
per adult
84% of travellers recommend
Siesta Key, FL - Clear Kayak LED Night Glass Bottom 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.