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Siesta Key Vacation Packages

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Siesta Key Flight + Hotel Packages

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

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $776, price is now $507 per person
$507
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) 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 Lido Beach and Siesta Key Beach are located nearby.
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,349, price is now $804 per person
$804
per person
Sep 2 - Sep 6
found 2 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,191, price is now $720 per person
$720
per person
Sep 8 - Sep 13
found 4 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) 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 Beach Walk are located nearby.
Waterfront Resort Condo Gulf Sun Set

Waterfront Resort Condo Gulf Sun Set

3 out of 5
Save 100% on your flight
Price was $1,589, price is now $971 per person
$971
per person
Jul 21 - Jul 27
found 4 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Tampa (TPA)
Stay at this aparthotel in Dunedin. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $1,132, price is now $705 per person
$705
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) 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.
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,080, price is now $1,297 per person
$1,297
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) to Tampa (TPA)
Book a stay at this beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,679, price is now $1,078 per person
$1,078
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) 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.
Villa Valentino Luxury 8BR Villa & Pool

Villa Valentino Luxury 8BR Villa & Pool

3 out of 5
Save 100% on your flight
Price was $3,480, price is now $2,233 per person
$2,233
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Stay at this villa in Palm Harbor. Enjoy free WiFi, free parking, and a garden. Popular attractions Curlew Crossing Shopping Center and Dunedin Golf Club are located nearby.

Siesta Key Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $898, price is now $534 per person
$534
per person
Sep 2 - Sep 6
found 2 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,349, price is now $804 per person
$804
per person
Sep 2 - Sep 6
found 2 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Tampa (TPA)
Villa Valentino Luxury 8BR Villa & Pool

Villa Valentino Luxury 8BR Villa & Pool

3 out of 5
Allen's Ridge
Save 100% on your flight
Price was $3,480, price is now $2,233 per person
$2,233
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
Price was $814, price is now $536 per person
$536
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)

Siesta Key Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $1,132, price is now $705 per person
$705
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,191, price is now $720 per person
$720
per person
Sep 8 - Sep 13
found 4 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Tampa (TPA)
Waterfront Resort Condo Gulf Sun Set

Waterfront Resort Condo Gulf Sun Set

3 out of 5
Save 100% on your flight
Price was $1,589, price is now $971 per person
$971
per person
Jul 21 - Jul 27
found 4 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,080, price is now $1,297 per person
$1,297
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) to Tampa (TPA)

Top Flight Deals

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

JetBlue Airways
Fri, Jul 24 - Mon, Jul 27
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, Jul 24 from Logan Intl. to Sarasota-Bradenton Intl., returning Mon, Jul 27, priced at $217 just found
Delta
Sat, Sep 26 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$219 Roundtrip, found 2 hours ago
$219
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Sep 26 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 30, priced at $219 found 2 hours ago
United
Tue, Oct 20 - Thu, Nov 19
DTW
Detroit Metropolitan Wayne County
SRQ
Sarasota-Bradenton Intl.
$259 Roundtrip, found 6 days ago
$259
Roundtrip
found 6 days ago
Select United flight, departing Tue, Oct 20 from Detroit Metropolitan Wayne County to Sarasota-Bradenton Intl., returning Thu, Nov 19, priced at $259 found 6 days ago
American Airlines
Tue, Nov 10 - Wed, Nov 18
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$261 Roundtrip, found 4 days ago
$261
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Nov 10 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Nov 18, priced at $261 found 4 days ago