Gillespie Park Vacations from $506

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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.
Hilton St. Petersburg Carillon Park

Hilton St. Petersburg Carillon Park

3.5 out of 5
Price was $847, price is now $506 per person
$506
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,013 reviews)
The room was spacious, clean, and quite.

Reviewed on Oct 26, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was $2,667, price is now $1,357 per person
$1,357
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (466 reviews)
Overall the property was clean; however, it was a great disappointment to see the street light with wires as an ocean view literally right outside your balcony. I also didn’t appreciate upon greeting the staff stressed about the fees instead of stressing what is already included, such as the beach chairs, umbrella etc…

Reviewed on Oct 15, 2025

DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
Rocky Point
Save 100% on your flight
Price was $1,340, price is now $754 per person
$754
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
8.2/10 Very Good! (1,019 reviews)
Everyone was really nice and helpful. Rooms were great.

Reviewed on Oct 27, 2025

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Save 100% on your flight
Price was $1,256, price is now $713 per person
$713
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
7/10 Good! (1,698 reviews)
The hotel has clean room, nice staff and perfect location, but the A/C make a lots of noise room 340.

Reviewed on Oct 25, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,281, price is now $801 per person
$801
per person
Jan 16 - Jan 19
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (669 reviews)
Fantastic! All around, the views were amazing. Amazing! The room was clean. Very well decorated super upscale. Just amazing.

Reviewed on Oct 27, 2025

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
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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

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $88 total per night from Oct 30 to Oct 31
$88 total
Oct 30 - Oct 31
Total with taxes and fees
9/10 Wonderful! (4,541 reviews)
This hotel was one for the books for my boyfriend and I. first saty here and we're already looking forward to our next stay. Location, staff, comfortability, safety, cleanliness and everything in-between was amazing!!

Reviewed on Oct 27, 2025

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
$147 nightly
The price is $166 total per night from Oct 29 to Oct 30
$166 total
Oct 29 - Oct 30
Total with taxes and fees
9.2/10 Wonderful! (5,058 reviews)
The property is stunning, A pool with three waterfalls turf lounging. Tiki huts. The staff incredibly friendly & accommodating. Beach is in walking distance. I would come back again & again. Oh the Room perfect Tropical, clean, comfy bed.

Reviewed on Oct 25, 2025

Tropical Beach Resorts
Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

3 out of 5
6600 S Tamiami Trl, Sarasota, FL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $120 total per night from Nov 4 to Nov 5
$120 total
Nov 4 - Nov 5
Total with taxes and fees
8.2/10 Very Good! (1,797 reviews)
The pool was the perfect temperature and the bar staff was very nice.

Reviewed on Oct 27, 2025

Spark by Hilton Sarasota Siesta Key Gateway
See all 14,247 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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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
Mall at University Town Center

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
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

Things to do

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

$55
per adult
88% 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
74% 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
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.