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Siesta Key Vacation Packages

Build your package with 2 more options

Siesta Key Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Price was $474, price is now $334 per person
$334
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this historic hotel in Tampa. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tampa Riverwalk and Benchmark International Arena are located nearby.

The Knickerbocker by Delphius

The Knickerbocker by Delphius

3 out of 5
Price was $3,098, price is now $1,985 per person
$1,985
per person
Jan 6 - Jan 11
found 12 hours ago
Roundtrip flight included
Hartford (BDL) 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.

Landing Palmetto Apartments

Landing Palmetto Apartments

4.5 out of 5
Save 100% on your flight
Price was $1,363, price is now $885 per person
$885
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this luxury aparthotel in Palmetto. Enjoy free WiFi, free parking, and 2 outdoor pickleball courts. Popular attractions Moccasin Wallow Golf Club and Andersen Race Park are located nearby.
Great location. We were in town for a wedding close to restaurants highway and all that we needed

Reviewed on Nov 1, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $1,190, price is now $802 per person
$802
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $568, price is now $394 per person
$394
per person
Dec 19 - Dec 23
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

Crystal Palms Beach Resort

Crystal Palms Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,310, price is now $923 per person
$923
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach apartment in Treasure Island. Enjoy free WiFi, free parking, and beach cabanas (surcharge). Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,215, price is now $860 per person
$860
per person
Jan 14 - Jan 17
found 17 hours ago
Roundtrip non-stop flight included
Hartford (BDL) 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.

Prestige Collection, Hotel Boutique & Spa

Prestige Collection, Hotel Boutique & Spa

2 out of 5
Price was $490, price is now $347 per person
$347
per person
Jan 8 - Jan 11
found 21 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Stay at this hotel in St. Petersburg. Enjoy free WiFi, daily housekeeping, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Tampa Bay and Vinoy Park are located nearby.

Siesta Key Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
Virginia Park
Price was $461, price is now $321 per person
$321
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $1,190, price is now $802 per person
$802
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
La Tortuga Historic Downtown Pass A Grille

La Tortuga Historic Downtown Pass A Grille

4 out of 5
Pass-a-Grille
Price was $1,263, price is now $867 per person
$867
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $568, price is now $394 per person
$394
per person
Dec 19 - Dec 23
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)

Siesta Key Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,315, price is now $801 per person
$801
per person
Jan 10 - Jan 16
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $1,581, price is now $855 per person
$855
per person
Jan 15 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Price was $3,086, price is now $1,892 per person
$1,892
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,717, price is now $1,077 per person
$1,077
per person
Jan 8 - Jan 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Tue, Jan 19 - Sat, Feb 6
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$199 Roundtrip, found 2 hours ago
$199
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Jan 19 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Sat, Feb 6, priced at $199 found 2 hours ago
Delta
Tue, Jan 5 - Sat, Jan 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$209 Roundtrip, found 8 hours ago
$209
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Jan 5 from Logan Intl. to Sarasota-Bradenton Intl., returning Sat, Jan 9, priced at $209 found 8 hours ago
United
Tue, Jan 19 - Tue, Feb 2
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$219 Roundtrip, just found
$219
Roundtrip
just found
Select United flight, departing Tue, Jan 19 from LaGuardia to Sarasota-Bradenton Intl., returning Tue, Feb 2, priced at $219 just found
Southwest Airlines
Fri, Jan 1 - Wed, Jan 6
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$223 Roundtrip, found 7 hours ago
$223
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Fri, Jan 1 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Wed, Jan 6, priced at $223 found 7 hours ago