Cheap Vacations in Siesta Key

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Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
Price was $621, price is now $413 per person
$413
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $1,405, price is now $881 per person
$881
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $734, price is now $510 per person
$510
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)

3-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 $476, price is now $283 per person
$283
per person
Jan 29 - Feb 1
found 17 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Save 100% on your flight
Price was $636, price is now $398 per person
$398
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $1,405, price is now $881 per person
$881
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $741, price is now $481 per person
$481
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Longboat Bay Club

Longboat Bay Club

3.5 out of 5
Save 100% on your flight
Price was $1,001, price is now $650 per person
$650
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
Sirata St. Pete Beach

Sirata St. Pete Beach

3 out of 5
Save 100% on your flight
Price was $456, price is now $301 per person
$301
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
Price was $621, price is now $413 per person
$413
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Holiday Inn Express Sarasota East - I-75 by IHG

Holiday Inn Express Sarasota East - I-75 by IHG

2.5 out of 5
Save 100% on your flight
Price was $579, price is now $385 per person
$385
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $881, price is now $604 per person
$604
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $710, price is now $489 per person
$489
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $734, price is now $510 per person
$510
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $522, price is now $365 per person
$365
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)

4-night Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
Zoo House Down Town Tampa

Zoo House Down Town Tampa

2.5 out of 5
Save 100% on your flight
Price was $449, price is now $309 per person
$309
per person
Jan 16 - Jan 20
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Save 100% on your flight
Price was $1,903, price is now $1,143 per person
$1,143
per person
Jan 8 - Jan 12
found 16 hours ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $2,052, price is now $1,248 per person
$1,248
per person
Jan 8 - Jan 12
found 16 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Price was $857, price is now $535 per person
$535
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $977, price is now $648 per person
$648
per person
Jan 8 - Jan 12
found 16 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $878, price is now $584 per person
$584
per person
Jan 8 - Jan 12
found 16 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $677, price is now $456 per person
$456
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $881, price is now $594 per person
$594
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $983, price is now $666 per person
$666
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $745, price is now $505 per person
$505
per person
Jan 8 - Jan 12
found 16 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Ramada by Wyndham Venice Hotel Venezia

Ramada by Wyndham Venice Hotel Venezia

3.5 out of 5
Save 100% on your flight
Price was $560, price is now $387 per person
$387
per person
Jan 8 - Jan 12
found 16 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
The Gemma by Brightwild

The Gemma by Brightwild

5 out of 5
Save 100% on your flight
Price was $4,731, price is now $3,279 per person
$3,279
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)

5-night Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
Sirata St. Pete Beach

Sirata St. Pete Beach

3 out of 5
Save 100% on your flight
Price was $679, price is now $406 per person
$406
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,997, price is now $1,018 per person
$1,018
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $904, price is now $495 per person
$495
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $896, price is now $498 per person
$498
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $796, price is now $456 per person
$456
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,396, price is now $812 per person
$812
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $2,728, price is now $1,592 per person
$1,592
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $913, price is now $537 per person
$537
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $1,079, price is now $638 per person
$638
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Save 100% on your flight
Price was $2,096, price is now $1,319 per person
$1,319
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,045, price is now $683 per person
$683
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,268, price is now $853 per person
$853
per person
Jan 15 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 $883, price is now $506 per person
$506
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,068, price is now $579 per person
$579
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $910, price is now $517 per person
$517
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 $3,434, price is now $2,006 per person
$2,006
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
Price was $1,097, price is now $644 per person
$644
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,480, price is now $906 per person
$906
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,481, price is now $921 per person
$921
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Turtle Beach Resort

Turtle Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,459, price is now $1,531 per person
$1,531
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $934, price is now $584 per person
$584
per person
Jan 4 - Jan 10
found 19 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Holiday Inn Express Sarasota East - I-75 by IHG

Holiday Inn Express Sarasota East - I-75 by IHG

2.5 out of 5
Save 100% on your flight
Price was $803, price is now $510 per person
$510
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Save 100% on your flight
Price was $1,311, price is now $837 per person
$837
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Sarasota (SRQ)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
Price was $1,172, price is now $758 per person
$758
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)

Flight deals to Siesta Key

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

Fri, Jan 9 - Mon, Jan 12
BOS
Boston
SRQ
Sarasota
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Jan 9 from Boston to Sarasota, returning Mon, Jan 12, priced at $137 found 2 days ago
Sat, Jan 10 - Sat, Jan 17
ORD
Chicago
SRQ
Sarasota
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jan 10 from Chicago to Sarasota, returning Sat, Jan 17, priced at $145 found 1 day ago
Sun, Jan 25 - Wed, Feb 4
JFK
New York
SRQ
Sarasota
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sun, Jan 25 from New York to Sarasota, returning Wed, Feb 4, priced at $147 found 6 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
2.62 mi from city center
$155 nightly
The price is $175 total per night
$175 total
Dec 7 - Dec 8
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
$247 nightly
The price is $279 total per night
$279 total
Dec 7 - Dec 8
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
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
6772 Sara Sea Circle Siesta Key FL
Free Cancellation
Reserve now, pay when you stay
2.68 mi from city center
$153 nightly
The price is $171 total per night
$171 total
Dec 7 - Dec 8
Total with taxes and fees
With a stay at Captiva Beach Resort in Siesta Key (South Village), you'll be within a 5-minute drive of Siesta Key Beach and Crescent Beach.
Pool
Kitchen
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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.