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Siesta Key vacations

Prices and availability subject to change. Additional terms may apply.
The Avalon Club

The Avalon Club

4 out of 5
per person
Jun 8 - Jun 13
Roundtrip non-stop flight included
Chicago (CHI) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 20
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Belle Vista
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 8 - Jun 13
Roundtrip non-stop flight included
Chicago (CHI) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 2
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 2
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Treasure Bay Resort & Marina

Treasure Bay Resort & Marina

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 20
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)

3-night Siesta Key vacations

Prices and availability subject to change. Additional terms may apply.
The Avalon Club

The Avalon Club

4 out of 5
per person
Jun 1 - Jun 4
Roundtrip flight included
Chicago (MDW) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 4
Roundtrip flight included
Chicago (MDW) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 10
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 10
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 10
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
May 31 - Jun 3
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 10
Roundtrip flight included
Houston (IAH) to Sarasota (SRQ)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 10
Roundtrip flight included
Houston (IAH) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 10
Roundtrip flight included
Houston (IAH) to Tampa (TPA)
Legacy Vacation Resorts - Indian Shores

Legacy Vacation Resorts - Indian Shores

3 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 10
Roundtrip flight included
Houston (IAH) to Tampa (TPA)
Nordvind Resort

Nordvind Resort

3 out of 5
Save 100% on your flight
per person
May 31 - Jun 3
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Barefoot Beach Club

Barefoot Beach Club

2.5 out of 5
Save 100% on your flight
per person
May 31 - Jun 3
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

4-night Siesta Key vacations

Prices and availability subject to change. Additional terms may apply.
The Avalon Club

The Avalon Club

4 out of 5
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
May 25 - May 29
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
May 25 - May 29
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 10
Roundtrip flight included
Houston (IAH) to Sarasota (SRQ)

5-night Siesta Key vacations

Prices and availability subject to change. Additional terms may apply.
The Avalon Club

The Avalon Club

4 out of 5
per person
Jun 8 - Jun 13
Roundtrip non-stop flight included
Chicago (CHI) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 20
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 20
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 8 - Jun 13
Roundtrip non-stop flight included
Chicago (CHI) to Tampa (TPA)
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Treasure Bay Resort & Marina

Treasure Bay Resort & Marina

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 20
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 20
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Sailport Waterfront Suites

Sailport Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)

6-7 night Siesta Key vacations

Prices and availability subject to change. Additional terms may apply.
The Avalon Club

The Avalon Club

4 out of 5
per person
May 26 - Jun 2
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 8
Roundtrip non-stop flight included
Houston (IAH) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 15
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 15
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 15
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 2
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 15
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 2
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
May 25 - May 31
Roundtrip flight included
Houston (IAH) to Sarasota (SRQ)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 2
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 8
Roundtrip non-stop flight included
Houston (IAH) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 15
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)

Flight deals to Siesta Key

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

Tue, Jun 11 - Tue, Jun 25
PHL
Philadelphia
SRQ
Sarasota
$71 Roundtrip, found 1 day ago
$71
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jun 11 from Philadelphia to Sarasota, returning Tue, Jun 25, priced at $71 found 1 day ago
Fri, May 10 - Sun, May 12
BOS
Boston
SRQ
Sarasota
$128 Roundtrip, found 16 hours ago
$128
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Fri, May 10 from Boston to Sarasota, returning Sun, May 12, priced at $128 found 16 hours ago
Sun, Jun 2 - Thu, Jun 13
JFK
New York
SRQ
Sarasota
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Jun 2 from New York to Sarasota, returning Thu, Jun 13, priced at $202 found 1 day ago

Top rated hotels for your Siesta Key vacation

Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Free Cancellation
Reserve now, pay when you stay
2.62 mi from city center
The price is $146 per night
$146
per night
Apr 28 - Apr 29
With a stay at Tropical Beach Resorts in Siesta Key, you'll be in the business district, within a 10-minute walk of Siesta Key Marina and Crescent Beach.
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 out of 5
5311 Ocean Blvd, Siesta Key, FL
0.12 mi from city center
The price is $207 per night
$207
per night
Apr 29 - Apr 30
With a stay at Siesta Key Beach Resort and Suites in Siesta Key (Siesta Key Village), you'll be a 1-minute drive from Siesta Key Beach and 6 minutes from Crescent Beach.
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
140 Columbus Blvd., Siesta Key, FL
0.1 mi from city center
The price is $284 per night
$284
per night
May 1 - May 2
With a stay at Tropical Breeze Resort in Siesta Key (Siesta Key Village), you'll be a 1-minute drive from Siesta Key Beach and 8 minutes from Sarasota Memorial Hospital.
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.