Cheap Vacations in Siesta Key

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Siesta Key vacations

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

The Avalon Club

4 out of 5
per person
Jun 18 - Jun 23
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Wesley Chapel South
Save 100% on your flight
per person
Jul 2 - Jul 9
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 30
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Downtown Tampa
Save 100% on your flight
per person
Jul 2 - Jul 9
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Coral Reef Beach Resort by VRI Americas

Coral Reef Beach Resort by VRI Americas

3.5 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip flight included
Chicago (ORD) 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 13 - Jun 17
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 11
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Save 100% on your flight
per person
Jun 13 - Jun 17
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 30
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
per person
Jun 17 - Jun 21
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

3-night Siesta Key vacations

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

The Avalon Club

4 out of 5
per person
Jun 14 - Jun 17
Roundtrip flight included
Philadelphia (PHL) 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 12 - Jun 15
Roundtrip 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 12 - Jun 15
Roundtrip flight included
Chicago (ORD) 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
Jul 9 - Jul 12
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Coral Reef Beach Resort by VRI Americas

Coral Reef Beach Resort by VRI Americas

3.5 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip 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 12 - Jun 15
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 19
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
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 13 - Jun 16
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 12
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

4-night Siesta Key vacations

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

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 6
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
per person
Jul 3 - Jul 7
Roundtrip non-stop flight included
Indianapolis (IND) 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 13 - Jun 17
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 17
Roundtrip non-stop flight included
Indianapolis (IND) 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
Jul 3 - Jul 7
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
per person
Jun 17 - Jun 21
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
per person
Jun 13 - Jun 17
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 17
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 17
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
per person
Jul 3 - Jul 7
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 17
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Beach House Suites by the Don CeSar

Beach House Suites by the Don CeSar

3 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 17
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)

5-night Siesta Key vacations

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

The Avalon Club

4 out of 5
per person
Jun 18 - Jun 23
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 27 - Jul 2
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
per person
Jun 27 - Jul 2
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jun 27 - Jul 2
Roundtrip flight included
Boston (BOS) 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 18 - Jun 23
Roundtrip flight included
Boston (BOS) 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 27 - Jul 2
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Sirata Beach Resort

Sirata Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 27 - Jul 2
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jun 18 - Jun 23
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Shephard's Beach Resort

Shephard's Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 10
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Courtyard by Marriott Clearwater Beach

Courtyard by Marriott Clearwater Beach

3 out of 5
per person
Jun 18 - Jun 23
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
AC Hotel Clearwater Beach

AC Hotel Clearwater Beach

3 out of 5
per person
Jun 18 - Jun 23
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Barefoot Beach Club

Barefoot Beach Club

2.5 out of 5
Save 100% on your flight
per person
Jun 27 - Jul 2
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

6-7 night Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
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
Jul 2 - Jul 9
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 30
Roundtrip flight included
Boston (BOS) 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
Jul 2 - Jul 9
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 9
Roundtrip non-stop flight included
Boston (BOS) 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
Jul 2 - Jul 9
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 9
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 30
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Sailport Waterfront Suites

Sailport Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 9
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 9
Roundtrip non-stop flight included
Boston (BOS) 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 24 - Jun 30
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
La Quinta Inn & Suites by Wyndham USF (Near Busch Gardens)

La Quinta Inn & Suites by Wyndham USF (Near Busch Gardens)

2.5 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 9
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 9
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)

Flight deals to Siesta Key

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

Sun, Jul 28 - Thu, Aug 15
PHL
Philadelphia
SRQ
Sarasota
$88 Roundtrip, found 5 days ago
$88
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Jul 28 from Philadelphia to Sarasota, returning Thu, Aug 15, priced at $88 found 5 days ago
Tue, Aug 27 - Wed, Sep 11
JFK
New York
SRQ
Sarasota
$147 Roundtrip, found 22 hours ago
$147
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Tue, Aug 27 from New York to Sarasota, returning Wed, Sep 11, priced at $147 found 22 hours ago
Thu, May 30 - Sat, Jun 8
ORD
Chicago
SRQ
Sarasota
$158 Roundtrip, found 6 days ago
$158
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, May 30 from Chicago to Sarasota, returning Sat, Jun 8, priced at $158 found 6 days ago

Top rated hotels for your Siesta Key vacation

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 $197 per night
$197
per night
May 27 - May 28
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.
Pool
Pet friendly
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 $145 per night
$145
per night
May 22 - May 23
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.
Pool
Parking included
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 $262 per night
$262
per night
May 28 - May 29
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.
Pool
Pet friendly
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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.