Search Deals on
Siesta Key Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

Siesta Key Public Beach showing a sandy beach

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.

Mar Bay Motel &Suites

2 out of 5

Save 100% on your flight

Price was $768, price is now $510 per person

$510

per person

May 3 - May 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this hotel in Safety Harbor. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions BayCare Ballpark and Philippe Park are located nearby.

voco Sarasota by IHG

3.5 out of 5

Save 100% on your flight

Price was $1,196, price is now $722 per person

$722

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this business-friendly hotel in Sarasota. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.

The Westin Sarasota

4 out of 5

Save 100% on your flight

Price was $1,597, price is now $1,010 per person

$1,010

per person

May 1 - May 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.

Ocean Club Treasure Island Hotel

4 out of 5

Price was $1,173, price is now $776 per person

$776

per person

Jun 4 - Jun 8

found 12 hours ago

Roundtrip non-stop 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.

Captiva Beach Resort

3 out of 5

Save 100% on your flight

Price was $1,051, price is now $711 per person

$711

per person

May 25 - May 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Hilton Garden Inn Tampa Northwest/Oldsmar

3 out of 5

Price was $830, price is now $586 per person

$586

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this business-friendly hotel in Oldsmar. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Oldsmar Flea Market and Tampa Bay Downs are located nearby.

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5

Save 100% on your flight

Price was $1,115, price is now $794 per person

$794

per person

Jun 8 - Jun 12

found 7 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, 3 outdoor pools, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.