Cheap Vacations in Siesta Key

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Siesta Key vacations

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

Tropical Breeze Resort

3 out of 5
Siesta Key Village
Save 100% on your flight
Price was $1,211, price is now $903 per person
$903
per person
Mar 16 - Mar 19
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 $1,989, price is now $1,465 per person
$1,465
per person
Mar 12 - Mar 15
found 15 hours 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.
Lemon Bay Motel

Lemon Bay Motel

2 out of 5
Price was $435, price is now $310 per person
$310
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $788, price is now $498 per person
$498
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $1,841, price is now $1,181 per person
$1,181
per person
Mar 12 - Mar 15
found 15 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $881, price is now $613 per person
$613
per person
Mar 16 - Mar 19
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 $1,108, price is now $775 per person
$775
per person
Mar 16 - Mar 19
found 1 day 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 $883, price is now $623 per person
$623
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $629, price is now $446 per person
$446
per person
Mar 16 - Mar 19
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 $2,133, price is now $1,517 per person
$1,517
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $733, price is now $525 per person
$525
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
Save 100% on your flight
Price was $873, price is now $629 per person
$629
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Price was $688, price is now $501 per person
$501
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
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 $1,989, price is now $1,465 per person
$1,465
per person
Mar 12 - Mar 15
found 15 hours 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.
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
Save 100% on your flight
Price was $630, price is now $400 per person
$400
per person
Mar 12 - Mar 16
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 $1,190, price is now $720 per person
$720
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $2,035, price is now $1,235 per person
$1,235
per person
Mar 12 - Mar 16
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 $834, price is now $521 per person
$521
per person
Mar 12 - Mar 16
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 $807, price is now $524 per person
$524
per person
Mar 11 - Mar 15
found 13 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Save 100% on your flight
Price was $693, price is now $472 per person
$472
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $800, price is now $547 per person
$547
per person
Mar 12 - Mar 16
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 $3,163, price is now $2,173 per person
$2,173
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop 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 $1,079, price is now $744 per person
$744
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,920, price is now $1,356 per person
$1,356
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
Lemon Bay Motel

Lemon Bay Motel

2 out of 5
Price was $578, price is now $408 per person
$408
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Save 100% on your flight
Price was $1,779, price is now $1,263 per person
$1,263
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)

5-night Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
Save 100% on your flight
Price was $722, price is now $454 per person
$454
per person
Mar 11 - Mar 16
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
Price was $1,387, price is now $684 per person
$684
per person
Mar 11 - Mar 16
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 $875, price is now $532 per person
$532
per person
Mar 9 - Mar 14
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 $1,252, price is now $771 per person
$771
per person
Mar 11 - Mar 16
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 $992, price is now $616 per person
$616
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $2,395, price is now $1,503 per person
$1,503
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $845, price is now $540 per person
$540
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $935, price is now $600 per person
$600
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Save 100% on your flight
Price was $821, price is now $527 per person
$527
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
Save 100% on your flight
Price was $703, price is now $466 per person
$466
per person
Mar 9 - Mar 14
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 $2,076, price is now $1,397 per person
$1,397
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,512, price is now $1,018 per person
$1,018
per person
Mar 9 - Mar 14
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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $978, price is now $602 per person
$602
per person
Mar 26 - Apr 1
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 $1,434, price is now $717 per person
$717
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,780, price is now $975 per person
$975
per person
Mar 16 - Mar 22
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 $2,563, price is now $1,528 per person
$1,528
per person
Mar 18 - Mar 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,598, price is now $1,038 per person
$1,038
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,522, price is now $997 per person
$997
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
Save 100% on your flight
Price was $1,396, price is now $930 per person
$930
per person
Mar 7 - Mar 14
found 6 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $1,299, price is now $866 per person
$866
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Save 100% on your flight
Price was $1,262, price is now $854 per person
$854
per person
Mar 26 - Apr 1
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $1,461, price is now $989 per person
$989
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $2,134, price is now $1,456 per person
$1,456
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,346, price is now $928 per person
$928
per person
Mar 26 - Apr 1
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 23 - Thu, Mar 5
PHL
Philadelphia
SRQ
Sarasota
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Philadelphia to Sarasota, returning Thu, Mar 5, priced at $98 found 1 day ago
Sat, Mar 7 - Wed, Mar 11
EWR
New York
SRQ
Sarasota
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select United flight, departing Sat, Mar 7 from New York to Sarasota, returning Wed, Mar 11, priced at $167 found 2 days ago
Fri, Feb 20 - Wed, Feb 25
BOS
Boston
SRQ
Sarasota
$173 Roundtrip, found 5 days ago
$173
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Feb 20 from Boston to Sarasota, returning Wed, Feb 25, priced at $173 found 5 days 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
$266 nightly
The price is $300 total per night
$300 total
Feb 10 - Feb 11
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
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
$226 nightly
The price is $255 total per night
$255 total
Feb 8 - Feb 9
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
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
$498 nightly
The price is $563 total per night
$563 total
Feb 6 - Feb 7
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
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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.