Search stays

Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 15
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
per person
Jul 3 - Jul 7
found 21 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 6
found 1 day ago
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
Belle Vista
Save 100% on your flight
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
Save 100% on your flight
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Save 100% on your flight
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop 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
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Sarasota (SRQ)
Postcard Inn On The Beach

Postcard Inn On The Beach

3 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 16
found 7 hours ago
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 16
found 7 hours ago
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)

3-night Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Tampa Central

La Quinta Inn & Suites by Wyndham Tampa Central

2.5 out of 5
per person
Jul 19 - Jul 22
found 9 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 15
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Sarasota (SRQ)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Sirata Beach Resort

Sirata Beach Resort

3 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 15
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 28 - Jul 1
found 18 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Clearwater Beach Marriott Suites on Sand Key

Clearwater Beach Marriott Suites on Sand Key

4 out of 5
Save 100% on your flight
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 15
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Sheraton Sand Key Resort

Sheraton Sand Key Resort

4 out of 5
Save 100% on your flight
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Hampton Inn & Suites Clearwater Beach

Hampton Inn & Suites Clearwater Beach

3.5 out of 5
Save 100% on your flight
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)

4-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 5 - Jul 9
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
per person
Jul 3 - Jul 7
found 21 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
found 21 hours ago
Roundtrip flight included
Philadelphia (PHL) 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
Jul 4 - Jul 8
found 21 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 16
found 7 hours ago
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 16
found 7 hours ago
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)
Postcard Inn On The Beach

Postcard Inn On The Beach

3 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
found 21 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
La Tortuga

La Tortuga

4 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 16
found 7 hours ago
Roundtrip flight included
Chicago (CHI) 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
found 21 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
found 21 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Sirata Beach Resort

Sirata Beach Resort

3 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 16
found 7 hours ago
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)

5-night Siesta Key vacations

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
Save 100% on your flight
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
per person
Jul 2 - Jul 7
found 1 day ago
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
Jul 1 - Jul 6
found 1 day ago
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
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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
Jul 1 - Jul 6
found 1 day ago
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
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop 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 2 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 1 - Jul 6
found 1 day ago
Roundtrip non-stop 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
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop 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
Jul 4 - Jul 9
found 19 hours ago
Roundtrip non-stop flight included
Omaha (OMA) to Sarasota (SRQ)

6-7 night Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
ZenHomes

ZenHomes

3 out of 5
per person
Jul 8 - Jul 14
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 1 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 1 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 1 - Jul 7
found 1 day ago
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
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Pointe Condos by Barsala

The Pointe Condos by Barsala

4.5 out of 5
Save 100% on your flight
per person
Jul 8 - Jul 14
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 1 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
La Quinta Inn by Wyndham Tampa Near Busch Gardens

La Quinta Inn by Wyndham Tampa Near Busch Gardens

2.5 out of 5
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
La Quinta Inn & Suites by Wyndham Tampa Brandon Regency Park

La Quinta Inn & Suites by Wyndham Tampa Brandon Regency Park

2.5 out of 5
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Chase Suite Hotel Rocky Point Tampa

Chase Suite Hotel Rocky Point Tampa

3 out of 5
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

3.5 out of 5
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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, Jul 9 - Tue, Jul 16
PHL
Philadelphia
SRQ
Sarasota
$68 Roundtrip, found 4 days ago
$68
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Jul 9 from Philadelphia to Sarasota, returning Tue, Jul 16, priced at $68 found 4 days ago
Sat, Jul 20 - Sat, Jul 27
EWR
Newark
SRQ
Sarasota
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jul 20 from Newark to Sarasota, returning Sat, Jul 27, priced at $145 found 1 day ago
Wed, Jun 12 - Tue, Jun 18
JFK
New York
SRQ
Sarasota
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Jun 12 from New York to Sarasota, returning Tue, Jun 18, priced at $147 found 2 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 30 - May 31
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 $260 per night
$260
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
Don't see what you're looking for?
See all available properties in Siesta Key
View all properties
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.