Cherokee Park Vacations from $657

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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.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$657

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,004 reviews)

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$739

per person

Oct 7 - Oct 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,160 reviews)

Good stay.

Reviewed on Sep 4, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$735

per person

Nov 6 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,173 reviews)

Loved the place, I was so impressed how clean it was. Beach view is perfect.

Reviewed on Sep 4, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,527

per person

Oct 17 - Oct 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (584 reviews)

The room was immaculate and the beds and pillows were the comfiest I have ever slept in. The room had everything we needed to make our stay comfortable. The location is perfect and the beach there is amazing. We have stayed here 4 times now and will be back again. This is a small, locally owned resort and they take great pride in the property. We absolutely love it.

Reviewed on Sep 3, 2026

Captiva Beach Resort

South Village

Save 100% on your flight

$870

per person

Oct 17 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,303 reviews)

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

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.

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.

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.

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.

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.

Cherokee Park Hotel Deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Fully refundableReserve now, pay when you stay

$62 nightly

$71 total

Sep 9 - Sep 10

Total with taxes and fees

9.2/10 Wonderful! (5,955 reviews)

"Clean & nice property"

Reviewed on Sep 5, 2026

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Fully refundableReserve now, pay when you stay

$169 nightly

$191 total

Sep 13 - Sep 14

Total with taxes and fees

9.4/10 Exceptional! (2,539 reviews)

"The hotel was very clean spacious rooms and the staff were very friendly. The breakfast buffet that was included was wonderful with something for everyone. HOWEVER, the main reason we went (get away) was to enjoy the pool BUT the pool was filthy - bottom and top of water. Suggestion - maybe have ..."

Reviewed on Sep 5, 2026

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Fully refundableReserve now, pay when you stay

$158 nightly

$179 total

Sep 7 - Sep 8

Total with taxes and fees

9.4/10 Exceptional! (5,836 reviews)

"I loved this resort, very nice kept place. Beach area was amazing, white sand, calm and clear blue water. Pool Was beautiful as well."

Reviewed on Sep 5, 2026

See all 14,170 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.