Cheap Vacations in Longboat Key

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3-night Longboat 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 $652, price is now $464 per person
$464
per person
Jan 16 - Jan 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 $1,684, price is now $1,086 per person
$1,086
per person
Jan 15 - Jan 18
found 13 hours ago
Roundtrip flight included
Denver (DEN) 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 $2,203, price is now $1,451 per person
$1,451
per person
Jan 16 - Jan 19
found 17 hours ago
Roundtrip flight included
Denver (DEN) to Sarasota (SRQ)
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 $770, price is now $512 per person
$512
per person
Jan 16 - Jan 19
found 17 hours ago
Roundtrip flight included
Denver (DEN) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $757, price is now $505 per person
$505
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $988, price is now $674 per person
$674
per person
Jan 16 - Jan 19
found 6 hours ago
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $725, price is now $495 per person
$495
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $782, price is now $541 per person
$541
per person
Jan 16 - Jan 19
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 $808, price is now $582 per person
$582
per person
Jan 16 - Jan 19
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 $906, price is now $656 per person
$656
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Price was $681, price is now $496 per person
$496
per person
Jan 19 - Jan 22
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 $830, price is now $605 per person
$605
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)

4-night Longboat 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 $390, price is now $260 per person
$260
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Price was $1,599, price is now $909 per person
$909
per person
Jan 26 - Jan 30
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 $855, price is now $500 per person
$500
per person
Jan 26 - Jan 30
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
Save 100% on your flight
Price was $1,476, price is now $876 per person
$876
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $649, price is now $400 per person
$400
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $698, price is now $440 per person
$440
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $618, price is now $391 per person
$391
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Venice Beach Villas

Venice Beach Villas

3 out of 5
Save 100% on your flight
Price was $612, price is now $390 per person
$390
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $763, price is now $508 per person
$508
per person
Jan 21 - Jan 25
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 $427, price is now $290 per person
$290
per person
Jan 26 - Jan 30
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 $519, price is now $356 per person
$356
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $921, price is now $641 per person
$641
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)

5-night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $699, price is now $473 per person
$473
per person
Jan 12 - Jan 17
found 3 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Price was $2,881, price is now $1,598 per person
$1,598
per person
Jan 12 - Jan 17
found 3 hours 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
Save 100% on your flight
Price was $2,449, price is now $1,403 per person
$1,403
per person
Jan 12 - Jan 17
found 3 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,494, price is now $857 per person
$857
per person
Jan 15 - Jan 20
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $828, price is now $516 per person
$516
per person
Jan 12 - Jan 17
found 3 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $911, price is now $603 per person
$603
per person
Jan 14 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,198, price is now $825 per person
$825
per person
Jan 12 - Jan 17
found 3 hours ago
Roundtrip flight included
Cleveland (CLE) 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 $1,008, price is now $697 per person
$697
per person
Jan 12 - Jan 17
found 3 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $944, price is now $671 per person
$671
per person
Jan 15 - Jan 20
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,827, price is now $1,304 per person
$1,304
per person
Jan 15 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Sarasota (SRQ)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
Price was $790, price is now $571 per person
$571
per person
Jan 12 - Jan 17
found 3 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Siesta Palms By the Beach

Siesta Palms By the Beach

3.5 out of 5
Save 100% on your flight
Price was $673, price is now $498 per person
$498
per person
Jan 12 - Jan 17
found 3 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)

6-7 night Longboat Key vacations

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

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
Price was $1,183, price is now $768 per person
$768
per person
Jan 29 - Feb 5
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 $3,730, price is now $2,172 per person
$2,172
per person
Jan 12 - Jan 19
found 19 hours ago
Roundtrip 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 $1,799, price is now $1,101 per person
$1,101
per person
Jan 24 - Jan 31
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 $1,782, price is now $1,112 per person
$1,112
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,431, price is now $897 per person
$897
per person
Jan 7 - Jan 14
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $3,036, price is now $1,933 per person
$1,933
per person
Jan 18 - Jan 25
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,244, price is now $800 per person
$800
per person
Jan 17 - Jan 24
found 5 hours ago
Roundtrip non-stop flight included
Trenton (TTN) 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 $2,945, price is now $1,913 per person
$1,913
per person
Jan 12 - Jan 19
found 19 hours ago
Roundtrip flight included
Minneapolis (MSP) to Sarasota (SRQ)
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Save 100% on your flight
Price was $1,197, price is now $785 per person
$785
per person
Jan 12 - Jan 19
found 19 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $1,435, price is now $944 per person
$944
per person
Jan 29 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
Price was $1,291, price is now $850 per person
$850
per person
Jan 17 - Jan 24
found 5 hours ago
Roundtrip non-stop flight included
Trenton (TTN) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $1,904, price is now $1,270 per person
$1,270
per person
Jan 26 - Feb 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)

Flight deals to Longboat 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 4 days ago
$137
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Jan 9 from Boston to Sarasota, returning Mon, Jan 12, priced at $137 found 4 days ago
Sat, Jan 10 - Sat, Jan 17
ORD
Chicago
SRQ
Sarasota
$145 Roundtrip, found 2 days ago
$145
Roundtrip
found 2 days ago
Select United flight, departing Sat, Jan 10 from Chicago to Sarasota, returning Sat, Jan 17, priced at $145 found 2 days ago
Sun, Jan 25 - Tue, Feb 3
JFK
New York
SRQ
Sarasota
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Jan 25 from New York to Sarasota, returning Tue, Feb 3, priced at $148 found 1 day ago

Top rated hotels for your Longboat Key vacation

The St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

5 out of 5
1601 Gulf Of Mexico Drive Longboat Key FL
Free Cancellation
Reserve now, pay when you stay
5 mi from city center
$804 nightly
The price is $909 total per night
$909 total
Dec 8 - Dec 9
Total with taxes and fees
When you stay at The St. Regis Longboat Key Resort in Longboat Key, you'll be on the beach, a 5-minute drive from Mote Marine Laboratory & Aquarium and 6 minutes from Lido Beach.
On private beach
Pool
Zota Beach Resort

Zota Beach Resort

4 out of 5
4711 Gulf of Mexico Dr Longboat Key FL
Free Cancellation
Reserve now, pay when you stay
1.12 mi from city center
$269 nightly
The price is $304 total per night
$304 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
When you stay at Zota Beach Resort in Longboat Key, you'll be on the beach, within a 15-minute drive of Lido Beach and Coquina Beach.
On private beach
Pool
The Resort at Longboat Key Club

The Resort at Longboat Key Club

4 out of 5
220 Sands Point Road Longboat Key FL
Free Cancellation
Reserve now, pay when you stay
6.89 mi from city center
$499 nightly
The price is $564 total per night
$564 total
Dec 8 - Dec 9
Total with taxes and fees
When you stay at The Resort at Longboat Key Club in Longboat Key, you'll be by the ocean, within a 5-minute drive of Lido Beach and Mote Marine Laboratory & Aquarium.
On private beach
Pool
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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.