Cheap Vacations in Siesta Key

Choose two or more items and save on your trip:

Siesta Key vacations

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

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $1,330, price is now $921 per person
$921
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
South Village
Save 100% on your flight
Price was $2,332, price is now $1,624 per person
$1,624
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)

3-night Siesta Key vacations

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

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $600, price is now $386 per person
$386
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,309, price is now $843 per person
$843
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,533, price is now $1,013 per person
$1,013
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $762, price is now $504 per person
$504
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $626, price is now $417 per person
$417
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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
Price was $763, price is now $518 per person
$518
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,254, price is now $873 per person
$873
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $972, price is now $677 per person
$677
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Clearwater Beach Sheraton Resort on Sand Key

Clearwater Beach Sheraton Resort on Sand Key

4 out of 5
Save 100% on your flight
Price was $957, price is now $672 per person
$672
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Save 100% on your flight
Price was $1,051, price is now $738 per person
$738
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,994, price is now $1,411 per person
$1,411
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,272, price is now $908 per person
$908
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)

4-night Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
Lemon Bay Motel

Lemon Bay Motel

2 out of 5
Save 100% on your flight
Price was $438, price is now $280 per person
$280
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $536, price is now $311 per person
$311
per person
Feb 24 - Feb 28
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,186, price is now $719 per person
$719
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,397, price is now $861 per person
$861
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $767, price is now $486 per person
$486
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Residence Inn by Marriott Sarasota Bradenton

Residence Inn by Marriott Sarasota Bradenton

3 out of 5
Save 100% on your flight
Price was $901, price is now $598 per person
$598
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $3,631, price is now $2,457 per person
$2,457
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,330, price is now $921 per person
$921
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Save 100% on your flight
Price was $2,332, price is now $1,624 per person
$1,624
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
Save 100% on your flight
Price was $1,348, price is now $947 per person
$947
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $1,082, price is now $761 per person
$761
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,277, price is now $900 per person
$900
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)

5-night Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
Weathered The Storm

Weathered The Storm

3 out of 5
Save 100% on your flight
Price was $478, price is now $276 per person
$276
per person
Mar 1 - Mar 6
found 13 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,187, price is now $642 per person
$642
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,333, price is now $794 per person
$794
per person
Mar 8 - Mar 13
found 4 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $1,059, price is now $647 per person
$647
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $905, price is now $566 per person
$566
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

3 out of 5
Save 100% on your flight
Price was $523, price is now $330 per person
$330
per person
Mar 1 - Mar 6
found 14 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Beachview Inn Clearwater Beach

The Beachview Inn Clearwater Beach

3 out of 5
Save 100% on your flight
Price was $921, price is now $591 per person
$591
per person
Mar 1 - Mar 6
found 13 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Seffner Inn and Suites

Seffner Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $510, price is now $335 per person
$335
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Fairfield Inn & Suites by Marriott Sarasota Lakewood Ranch

Fairfield Inn & Suites by Marriott Sarasota Lakewood Ranch

2.5 out of 5
Save 100% on your flight
Price was $1,088, price is now $718 per person
$718
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $837, price is now $554 per person
$554
per person
Mar 1 - Mar 6
found 13 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,434, price is now $950 per person
$950
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $2,270, price is now $1,505 per person
$1,505
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)

6-7 night Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,262, price is now $757 per person
$757
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)
Landing Palmetto Apartments

Landing Palmetto Apartments

4 out of 5
Save 100% on your flight
Price was $1,532, price is now $1,078 per person
$1,078
per person
Mar 13 - Mar 19
found 1 day ago
Roundtrip flight included
Austin (AUS) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,541, price is now $850 per person
$850
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,622, price is now $940 per person
$940
per person
Mar 6 - Mar 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $2,049, price is now $1,237 per person
$1,237
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $2,358, price is now $1,447 per person
$1,447
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Save 100% on your flight
Price was $1,481, price is now $910 per person
$910
per person
Mar 6 - Mar 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,473, price is now $1,580 per person
$1,580
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Sarasota (SRQ)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,497, price is now $965 per person
$965
per person
Feb 17 - Feb 23
found 1 day ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
Save 100% on your flight
Price was $1,622, price is now $1,047 per person
$1,047
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,406, price is now $913 per person
$913
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Sarasota (SRQ)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $1,339, price is now $874 per person
$874
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)

Flight deals to Siesta Key

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

Mon, Feb 2 - Tue, Feb 3
JFK
New York
SRQ
Sarasota
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Feb 2 from New York to Sarasota, returning Tue, Feb 3, priced at $157 found 1 day ago
Mon, Feb 2 - Tue, Feb 3
EWR
New York
SRQ
Sarasota
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select United flight, departing Mon, Feb 2 from New York to Sarasota, returning Tue, Feb 3, priced at $157 found 1 day ago
Fri, Jan 30 - Sat, Jan 31
LGA
New York
SRQ
Sarasota
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jan 30 from New York to Sarasota, returning Sat, Jan 31, priced at $177 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
2.65 mi from city center
$189 nightly
The price is $214 total per night
$214 total
Jan 19 - Jan 20
Total with taxes and fees
Located in Siesta Key (South Village), Tropical Beach Resorts is within a 10-minute walk of Siesta Key Marina and Crescent Beach.
Pool
Kitchen
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
$257 nightly
The price is $290 total per night
$290 total
Jan 19 - Jan 20
Total with taxes and fees
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
Hot Tub
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
140 Columbus Blvd. Siesta Key FL
Free Cancellation
Reserve now, pay when you stay
0.1 mi from city center
$197 nightly
The price is $223 total per night
$223 total
Jan 20 - Jan 21
Total with taxes and fees
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
Hot Tub
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.