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
Price was $846, price is now $540 per person
$540
per person
Feb 22 - Feb 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,330, price is now $948 per person
$948
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Siesta Key Village
Price was $1,259, price is now $902 per person
$902
per person
Feb 22 - Feb 25
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,527, price is now $1,099 per person
$1,099
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

3-night Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Price was $504, price is now $360 per person
$360
per person
Feb 22 - Feb 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
Price was $1,384, price is now $813 per person
$813
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
Price was $846, price is now $540 per person
$540
per person
Feb 22 - Feb 25
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 $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)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,203, price is now $781 per person
$781
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
Price was $617, price is now $407 per person
$407
per person
Feb 22 - Feb 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Price was $940, price is now $643 per person
$643
per person
Feb 22 - Feb 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Price was $661, price is now $456 per person
$456
per person
Feb 22 - Feb 25
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
Price was $738, price is now $512 per person
$512
per person
Feb 22 - Feb 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $670, price is now $474 per person
$474
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,330, price is now $948 per person
$948
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Residence Inn by Marriott Sarasota Bradenton

Residence Inn by Marriott Sarasota Bradenton

3 out of 5
Price was $752, price is now $538 per person
$538
per person
Feb 22 - Feb 25
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.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $686, price is now $434 per person
$434
per person
Feb 24 - Feb 28
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 3 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Price was $1,223, price is now $753 per person
$753
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $2,951, price is now $1,823 per person
$1,823
per person
Feb 16 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
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)
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)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,502, price is now $1,015 per person
$1,015
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
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 19 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 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,124, price is now $782 per person
$782
per person
Mar 6 - Mar 10
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.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $725, price is now $464 per person
$464
per person
Feb 21 - Feb 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,813, price is now $1,058 per person
$1,058
per person
Feb 23 - Feb 28
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 $1,707, price is now $1,001 per person
$1,001
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $2,245, price is now $1,339 per person
$1,339
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,091, price is now $671 per person
$671
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip 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 $2,097, price is now $1,305 per person
$1,305
per person
Feb 23 - Feb 28
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 20 hours ago
Roundtrip flight included
Boston (BOS) 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 $1,344, price is now $861 per person
$861
per person
Feb 23 - Feb 28
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
Save 100% on your flight
Price was $1,112, price is now $718 per person
$718
per person
Feb 23 - Feb 28
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 $1,101, price is now $716 per person
$716
per person
Feb 23 - Feb 28
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 $919, price is now $608 per person
$608
per person
Feb 23 - Feb 28
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 $1,457, price is now $973 per person
$973
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Tampa (TPA)

6-7 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 $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)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $2,989, price is now $1,726 per person
$1,726
per person
Feb 17 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $2,319, price is now $1,385 per person
$1,385
per person
Feb 28 - Mar 7
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 $1,840, price is now $1,110 per person
$1,110
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Sarasota (SRQ)
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)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $2,770, price is now $1,716 per person
$1,716
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,730, price is now $1,075 per person
$1,075
per person
Feb 17 - Feb 23
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 $4,812, price is now $2,993 per person
$2,993
per person
Feb 28 - Mar 7
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 $1,298, price is now $839 per person
$839
per person
Feb 17 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,379, price is now $894 per person
$894
per person
Feb 21 - Feb 27
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

3 out of 5
Save 100% on your flight
Price was $1,483, price is now $970 per person
$970
per person
Feb 23 - Mar 2
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 $1,491, price is now $979 per person
$979
per person
Feb 17 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 4 hours ago
$157
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Mon, Feb 2 from New York to Sarasota, returning Tue, Feb 3, priced at $157 found 4 hours ago
Mon, Feb 2 - Tue, Feb 3
EWR
New York
SRQ
Sarasota
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Select United flight, departing Mon, Feb 2 from New York to Sarasota, returning Tue, Feb 3, priced at $157 found 4 hours ago
Fri, Jan 30 - Sat, Jan 31
LGA
New York
SRQ
Sarasota
$177 Roundtrip, found 4 hours ago
$177
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Jan 30 from New York to Sarasota, returning Sat, Jan 31, priced at $177 found 4 hours 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.