Cheap Vacations in Longboat Key

Choose two or more items and save on your trip:

3-night Longboat 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 $351, price is now $248 per person
$248
per person
Jan 15 - Jan 18
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Price was $1,528, price is now $852 per person
$852
per person
Jan 29 - Feb 1
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
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 1 day 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 $682, price is now $424 per person
$424
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Price was $576, price is now $377 per person
$377
per person
Jan 22 - Jan 25
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $703, price is now $470 per person
$470
per person
Jan 22 - Jan 25
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $945, price is now $644 per person
$644
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $588, price is now $417 per person
$417
per person
Jan 15 - Jan 18
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $680, price is now $482 per person
$482
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Price was $797, price is now $570 per person
$570
per person
Jan 22 - Jan 25
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $638, price is now $463 per person
$463
per person
Jan 22 - Jan 25
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Venice Beach Villas

Venice Beach Villas

3 out of 5
Price was $503, price is now $366 per person
$366
per person
Jan 29 - Feb 1
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)

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 12 - Jan 16
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Price was $1,601, price is now $909 per person
$909
per person
Jan 12 - Jan 16
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $869, price is now $500 per person
$500
per person
Jan 12 - Jan 16
found 16 hours ago
Roundtrip flight included
Detroit (DTW) 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 $1,886, price is now $1,092 per person
$1,092
per person
Jan 12 - Jan 16
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $722, price is now $448 per person
$448
per person
Jan 12 - Jan 16
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $620, price is now $391 per person
$391
per person
Jan 12 - Jan 16
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $794, price is now $526 per person
$526
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $412, price is now $278 per person
$278
per person
Jan 12 - Jan 16
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
Price was $659, price is now $448 per person
$448
per person
Jan 12 - Jan 16
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $884, price is now $601 per person
$601
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $522, price is now $356 per person
$356
per person
Jan 12 - Jan 16
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $707, price is now $485 per person
$485
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)

5-night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Save 100% on your flight
Price was $570, price is now $400 per person
$400
per person
Jan 28 - Feb 2
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $972, price is now $548 per person
$548
per person
Jan 28 - Feb 2
found 21 hours ago
Roundtrip flight included
Detroit (DTW) 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 $2,051, price is now $1,209 per person
$1,209
per person
Jan 15 - Jan 20
found 23 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Sarasota (SRQ)
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 $854, price is now $572 per person
$572
per person
Jan 28 - Feb 2
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Save 100% on your flight
Price was $640, price is now $437 per person
$437
per person
Jan 28 - Feb 2
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
Price was $799, price is now $553 per person
$553
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $738, price is now $511 per person
$511
per person
Jan 28 - Feb 2
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $695, price is now $487 per person
$487
per person
Jan 28 - Feb 2
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
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 $1,130, price is now $822 per person
$822
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,793, price is now $1,306 per person
$1,306
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
Price was $1,847, price is now $1,352 per person
$1,352
per person
Jan 28 - Feb 2
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,189, price is now $872 per person
$872
per person
Jan 28 - Feb 2
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)

6-7 night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
Magnuson Hotel Bradenton

Magnuson Hotel Bradenton

2.5 out of 5
Save 100% on your flight
Price was $375, price is now $244 per person
$244
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $1,116, price is now $619 per person
$619
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,324, price is now $742 per person
$742
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $2,230, price is now $1,282 per person
$1,282
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,233, price is now $739 per person
$739
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Save 100% on your flight
Price was $3,114, price is now $1,878 per person
$1,878
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $926, price is now $569 per person
$569
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $659, price is now $405 per person
$405
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Save 100% on your flight
Price was $1,042, price is now $643 per person
$643
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,314, price is now $812 per person
$812
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $693, price is now $450 per person
$450
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,100, price is now $715 per person
$715
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 3 days ago
$137
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Jan 9 from Boston to Sarasota, returning Mon, Jan 12, priced at $137 found 3 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 19 hours ago
$148
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Sun, Jan 25 from New York to Sarasota, returning Tue, Feb 3, priced at $148 found 19 hours 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
$489 nightly
The price is $553 total per night
$553 total
Dec 14 - Dec 15
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
Don't see what you're looking for?
See all available properties in Longboat Key
View all properties
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.