Cherokee Park Vacations from $494

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Your Cherokee Park Vacation

Reserving a Cherokee Park vacation package is a wonderful way to become familiar with this unique neighborhood. From its hot spots to its lesser-known delights, a world of discovery is waiting. When it's time to get out and explore, you'll find plenty of popular attractions nearby including St. Armands Circle, Marie Selby Botanical Gardens and Lido Beach. Visit one, two (or even all!) during your trip to Cherokee Park. Don't just think about it — make it happen! Lock in your ideal Cherokee Park vacation with Expedia and enjoy traveling your way.

The Latest Cherokee Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $937, price is now $494 per person
$494
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (59 reviews)
Close to downtown safety harbor, oldsmar and Clearwater, the perfect retreat being close to everything but not in the heart of it all.

Reviewed on May 12, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,277, price is now $745 per person
$745
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
Great overall experience. Already planning a return trip

Reviewed on Oct 3, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
South Village
Save 100% on your flight
Price was $2,313, price is now $1,350 per person
$1,350
per person
Nov 21 - Nov 25
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9.6/10 Exceptional! (290 reviews)
We celebrated my daughter’s 30th birthday and it was perfect. I can’t wait to stay again. The beach was truly amazing. This place has everything you need.

Reviewed on Sep 15, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,733, price is now $1,633 per person
$1,633
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (456 reviews)
Clean, quite, nice staff

Reviewed on Oct 6, 2025

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,405, price is now $886 per person
$886
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9.2/10 Wonderful! (301 reviews)
Nice location and great service

Reviewed on Oct 2, 2025

Where to stay in Cherokee Park

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

Cherokee 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
$57 nightly
The price is $64 total per night from Oct 7 to Oct 8
$64 total
Oct 7 - Oct 8
Total with taxes and fees
9/10 Wonderful! (4,408 reviews)
"Excellent!"

Reviewed on Oct 5, 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 7 to Oct 8
$166 total
Oct 7 - Oct 8
Total with taxes and fees
9.2/10 Wonderful! (5,008 reviews)
"Rooms very clean. Close to lots of places to eat."

Reviewed on Oct 1, 2025

Tropical Beach Resorts
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West, Bradenton, FL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $229 total per night from Oct 7 to Oct 8
$229 total
Oct 7 - Oct 8
Total with taxes and fees
9.4/10 Exceptional! (1,776 reviews)
"Nice pool and staff. Beautiful view out to the marina and close to Anna Maria."

Reviewed on Oct 2, 2025

Compass Hotel by Margaritaville Anna Maria Sound
See all 13,380 properties in Cherokee 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 Cherokee 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
Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

$99
per adult
Anna Maria Island & Bradenton Beach Parasailing 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.