Cheap Vacations in Siesta Key

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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 $877, price is now $585 per person
$585
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,128, price is now $795 per person
$795
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)

3-night Siesta Key vacations

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

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $714, price is now $466 per person
$466
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,014, price is now $651 per person
$651
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,253, price is now $812 per person
$812
per person
Feb 22 - Feb 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $877, price is now $585 per person
$585
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,040, price is now $701 per person
$701
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $709, price is now $488 per person
$488
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,083, price is now $750 per person
$750
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,033, price is now $724 per person
$724
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $740, price is now $520 per person
$520
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,128, price is now $795 per person
$795
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $668, price is now $477 per person
$477
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Save 100% on your flight
Price was $672, price is now $483 per person
$483
per person
Mar 3 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

4-night Siesta Key vacations

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

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $881, price is now $546 per person
$546
per person
Mar 7 - Mar 11
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,464, price is now $1,349 per person
$1,349
per person
Mar 1 - Mar 5
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $2,177, price is now $1,350 per person
$1,350
per person
Feb 17 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $841, price is now $554 per person
$554
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Save 100% on your flight
Price was $1,126, price is now $765 per person
$765
per person
Feb 21 - Feb 25
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,369, price is now $935 per person
$935
per person
Feb 17 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,048, price is now $1,401 per person
$1,401
per person
Feb 17 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Save 100% on your flight
Price was $870, price is now $603 per person
$603
per person
Feb 24 - Feb 28
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Price was $3,668, price is now $2,565 per person
$2,565
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,556, price is now $1,089 per person
$1,089
per person
Feb 17 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $1,592, price is now $1,115 per person
$1,115
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $1,074, price is now $754 per person
$754
per person
Feb 17 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)

5-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 $1,103, price is now $687 per person
$687
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,797, price is now $1,010 per person
$1,010
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,820, price is now $1,066 per person
$1,066
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,808, price is now $1,101 per person
$1,101
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,565, price is now $960 per person
$960
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $2,419, price is now $1,508 per person
$1,508
per person
Feb 26 - Mar 3
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,059, price is now $1,327 per person
$1,327
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,193, price is now $769 per person
$769
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,152, price is now $747 per person
$747
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,113, price is now $723 per person
$723
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,522, price is now $992 per person
$992
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
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 $1,343, price is now $877 per person
$877
per person
Feb 22 - Feb 27
found 1 day ago
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.
Lemon Bay Motel

Lemon Bay Motel

2 out of 5
Price was $653, price is now $331 per person
$331
per person
Feb 24 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $2,239, price is now $1,197 per person
$1,197
per person
Feb 24 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Price was $2,307, price is now $1,291 per person
$1,291
per person
Feb 24 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,329, price is now $776 per person
$776
per person
Feb 24 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $3,037, price is now $1,778 per person
$1,778
per person
Feb 24 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
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 $1,318, price is now $783 per person
$783
per person
Feb 24 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $1,023, price is now $624 per person
$624
per person
Mar 11 - Mar 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,527, price is now $934 per person
$934
per person
Mar 6 - Mar 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
Save 100% on your flight
Price was $840, price is now $520 per person
$520
per person
Feb 24 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $1,948, price is now $1,239 per person
$1,239
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $2,540, price is now $1,636 per person
$1,636
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $1,644, price is now $1,080 per person
$1,080
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)

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 hour ago
$157
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Mon, Feb 2 from New York to Sarasota, returning Tue, Feb 3, priced at $157 found 1 hour ago
Mon, Feb 2 - Tue, Feb 3
EWR
New York
SRQ
Sarasota
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select United flight, departing Mon, Feb 2 from New York to Sarasota, returning Tue, Feb 3, priced at $157 found 1 hour ago
Fri, Jan 30 - Sat, Jan 31
LGA
New York
SRQ
Sarasota
$177 Roundtrip, found 1 hour ago
$177
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Fri, Jan 30 from New York to Sarasota, returning Sat, Jan 31, priced at $177 found 1 hour 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
$206 nightly
The price is $233 total per night
$233 total
Jan 21 - Jan 22
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
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
$241 nightly
The price is $270 total per night
$270 total
Jan 19 - Jan 20
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
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
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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.