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 $681, price is now $478 per person
$478
per person
Jan 22 - Jan 25
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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
Price was $2,894, price is now $1,580 per person
$1,580
per person
Jan 23 - Jan 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $1,758, price is now $1,070 per person
$1,070
per person
Feb 6 - Feb 13
found 1 day ago
Roundtrip non-stop 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 $1,190, price is now $823 per person
$823
per person
Feb 6 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Siesta Key Inn

Siesta Key Inn

2 out of 5
South Village
Save 100% on your flight
Price was $2,005, price is now $1,391 per person
$1,391
per person
Feb 6 - Feb 13
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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $491, price is now $305 per person
$305
per person
Feb 9 - Feb 12
found 3 hours 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 $834, price is now $484 per person
$484
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,753, price is now $1,017 per person
$1,017
per person
Feb 9 - Feb 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

2.5 out of 5
Save 100% on your flight
Price was $510, price is now $347 per person
$347
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $644, price is now $440 per person
$440
per person
Jan 22 - Jan 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 $1,320, price is now $914 per person
$914
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
Price was $681, price is now $478 per person
$478
per person
Jan 22 - Jan 25
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $1,226, price is now $880 per person
$880
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $1,097, price is now $788 per person
$788
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop 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
Price was $1,095, price is now $788 per person
$788
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Arvilla

Arvilla

2 out of 5
Save 100% on your flight
Price was $734, price is now $533 per person
$533
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop 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 $620, price is now $453 per person
$453
per person
Feb 9 - Feb 12
found 3 hours 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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $695, price is now $418 per person
$418
per person
Feb 11 - Feb 15
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 $919, price is now $452 per person
$452
per person
Feb 11 - Feb 15
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 $2,050, price is now $1,207 per person
$1,207
per person
Jan 23 - Jan 27
found 20 hours ago
Roundtrip 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 $1,420, price is now $867 per person
$867
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,083, price is now $681 per person
$681
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $823, price is now $530 per person
$530
per person
Feb 6 - Feb 10
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 $973, price is now $648 per person
$648
per person
Jan 29 - Feb 2
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 $854, price is now $602 per person
$602
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Ramada by Wyndham Venice Hotel Venezia

Ramada by Wyndham Venice Hotel Venezia

3.5 out of 5
Save 100% on your flight
Price was $671, price is now $479 per person
$479
per person
Feb 6 - Feb 10
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 $1,839, price is now $1,315 per person
$1,315
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,238, price is now $886 per person
$886
per person
Feb 11 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
Siesta Key Inn

Siesta Key Inn

2 out of 5
Save 100% on your flight
Price was $1,015, price is now $737 per person
$737
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)

5-night Siesta Key vacations

Price found within the past 48 hours. Click for updated prices.
Ruskin Inn Hotel

Ruskin Inn Hotel

2.5 out of 5
Save 100% on your flight
Price was $537, price is now $367 per person
$367
per person
Jan 26 - Jan 31
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $875, price is now $375 per person
$375
per person
Feb 8 - Feb 13
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 $1,577, price is now $932 per person
$932
per person
Feb 8 - Feb 13
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,275, price is now $800 per person
$800
per person
Feb 8 - Feb 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Price was $942, price is now $636 per person
$636
per person
Jan 28 - Feb 2
found 24 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
Price was $914, price is now $620 per person
$620
per person
Jan 28 - Feb 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,049, price is now $712 per person
$712
per person
Jan 21 - Jan 26
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Bradenton Apartments by Landing

Bradenton Apartments by Landing

4.5 out of 5
Save 100% on your flight
Price was $1,305, price is now $889 per person
$889
per person
Feb 8 - Feb 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Save 100% on your flight
Price was $845, price is now $577 per person
$577
per person
Feb 5 - Feb 10
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $951, price is now $650 per person
$650
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $631, price is now $433 per person
$433
per person
Jan 21 - Jan 26
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Save 100% on your flight
Price was $597, price is now $412 per person
$412
per person
Jan 21 - Jan 26
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)

6-7 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
Save 100% on your flight
Price was $949, price is now $617 per person
$617
per person
Feb 6 - Feb 13
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 $1,543, price is now $694 per person
$694
per person
Feb 6 - Feb 13
found 1 day ago
Roundtrip non-stop 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
Price was $2,894, price is now $1,580 per person
$1,580
per person
Jan 23 - Jan 29
found 1 day 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 $1,719, price is now $1,035 per person
$1,035
per person
Feb 11 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,758, price is now $1,070 per person
$1,070
per person
Feb 6 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Bradenton Apartments by Landing

Bradenton Apartments by Landing

4.5 out of 5
Save 100% on your flight
Price was $1,792, price is now $1,137 per person
$1,137
per person
Feb 6 - Feb 13
found 1 day ago
Roundtrip non-stop 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 $1,658, price is now $1,067 per person
$1,067
per person
Feb 11 - Feb 18
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 $2,094, price is now $1,348 per person
$1,348
per person
Feb 6 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Landing Bradenton Near G.T. Bray Park

Landing Bradenton Near G.T. Bray Park

4 out of 5
Save 100% on your flight
Price was $1,841, price is now $1,188 per person
$1,188
per person
Feb 11 - Feb 18
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 $1,672, price is now $1,081 per person
$1,081
per person
Feb 6 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

2.5 out of 5
Price was $1,002, price is now $648 per person
$648
per person
Feb 4 - Feb 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Escape Coastal Resort on Casey Key

Escape Coastal Resort on Casey Key

2.5 out of 5
Save 100% on your flight
Price was $1,716, price is now $1,136 per person
$1,136
per person
Feb 6 - Feb 13
found 1 day ago
Roundtrip non-stop 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.

Sun, Jan 18 - Wed, Jan 21
EWR
New York
SRQ
Sarasota
$129 Roundtrip, found 5 days ago
$129
Roundtrip
found 5 days ago
Select United flight, departing Sun, Jan 18 from New York to Sarasota, returning Wed, Jan 21, priced at $129 found 5 days ago
Tue, Jan 20 - Fri, Jan 23
BOS
Boston
SRQ
Sarasota
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Jan 20 from Boston to Sarasota, returning Fri, Jan 23, priced at $137 found 5 days ago
Sat, Feb 7 - Sat, Feb 14
LGA
New York
SRQ
Sarasota
$201 Roundtrip, found 5 days ago
$201
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Feb 7 from New York to Sarasota, returning Sat, Feb 14, priced at $201 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
2.62 mi from city center
$147 nightly
The price is $166 total per night
$166 total
Dec 21 - Dec 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
$167 nightly
The price is $187 total per night
$187 total
Dec 21 - Dec 22
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
$270 nightly
The price is $305 total per night
$305 total
Jan 4 - Jan 5, 2026
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.