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Siesta Key Vacation Packages

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A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

Siesta Key
Florida
United States of America
North America
Hotwire.com

Siesta Key Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

The Knickerbocker by Delphius

3 out of 5

Save 100% on your flight

Price was $727, price is now $510 per person

$510

per person

Dec 24 - Dec 27

found 4 hours ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Book a stay at this business-friendly B&B in Tampa. Enjoy free WiFi, free parking, and 3 meeting rooms. Popular attractions Tampa Riverwalk and Benchmark International Arena are located nearby.

Ocean Club Treasure Island Hotel

4 out of 5

Save 100% on your flight

Price was $1,514, price is now $869 per person

$869

per person

Nov 17 - Nov 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

Room, pool and bar were amazing. My only complaint was beach too far to walk for afew of the others. Had to buy beach chairs as there were none at beach unless you paid a third party.

Reviewed on Oct 3, 2026

CW Resort

4 out of 5

Save 100% on your flight

Price was $2,682, price is now $1,732 per person

$1,732

per person

Dec 25 - Dec 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

The rooms are very nice and clean. There is a pleasant aroma when you enter the building and all through the resort. The food is excellent with excellent prices. I would definitely stay again.

Reviewed on Oct 2, 2026

Cedar Cove Resort and Cottages

3 out of 5

Save 100% on your flight

Price was $1,247, price is now $814 per person

$814

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.

Best place to stay on island!

Reviewed on Oct 1, 2026

Inn on the Beach - 18+ only

2.5 out of 5

Save 100% on your flight

Price was $904, price is now $601 per person

$601

per person

Dec 6 - Dec 11

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Book a stay at this beach motel in St. Pete Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Fort De Soto Park and Hurley Park are located nearby.

4BR Spacious Paradise

3 out of 5

Save 100% on your flight

Price was $1,462, price is now $986 per person

$986

per person

Nov 9 - Nov 16

found 17 hours ago

Roundtrip flight included

New York (NYC) to Tampa (TPA)

Stay at this apartment in Siesta Key. Enjoy free parking, a garden, and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5

Price was $774, price is now $535 per person

$535

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Everybody at the front desk was great and accommodating. It’s a basic room but has the features you need and a pool and walking distance to Siesta Key. It is not the Ritz Carlton, but it has what you need.

Reviewed on Oct 3, 2026

Calini Beach Club by Coolvacay

3 out of 5

Save 100% on your flight

Price was $2,247, price is now $1,564 per person

$1,564

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this condo in Siesta Key. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located nearby.