Cheap Vacations in Longboat Key

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Longboat Key vacations

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

Westwinds Waterfront Resort

3 out of 5
Price was $709, price is now $505 per person
$505
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Siesta Palms By the Beach

Siesta Palms By the Beach

3.5 out of 5
South Village
Save 100% on your flight
Price was $1,430, price is now $921 per person
$921
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,062, price is now $1,359 per person
$1,359
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Azul Resort

Azul Resort

2 out of 5
South Village
Save 100% on your flight
Price was $1,222, price is now $807 per person
$807
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Siesta Key Inn

Siesta Key Inn

2 out of 5
South Village
Save 100% on your flight
Price was $833, price is now $553 per person
$553
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,047, price is now $710 per person
$710
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,130, price is now $800 per person
$800
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,169, price is now $833 per person
$833
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Save 100% on your flight
Price was $844, price is now $602 per person
$602
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

4 out of 5
Save 100% on your flight
Price was $947, price is now $676 per person
$676
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)

3-night Longboat Key vacations

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

Innisbrook Resort

3.5 out of 5
Price was $670, price is now $485 per person
$485
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,062, price is now $1,359 per person
$1,359
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Siesta Key Inn

Siesta Key Inn

2 out of 5
Save 100% on your flight
Price was $833, price is now $553 per person
$553
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,047, price is now $710 per person
$710
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Westwinds Waterfront Resort

Westwinds Waterfront Resort

3 out of 5
Price was $709, price is now $505 per person
$505
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Save 100% on your flight
Price was $844, price is now $602 per person
$602
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

4 out of 5
Save 100% on your flight
Price was $947, price is now $676 per person
$676
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

4 out of 5
Save 100% on your flight
Price was $1,074, price is now $770 per person
$770
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $872, price is now $626 per person
$626
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $977, price is now $707 per person
$707
per person
Dec 2 - Dec 5
found 24 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Price was $769, price is now $556 per person
$556
per person
Dec 2 - Dec 5
found 24 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $696, price is now $504 per person
$504
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)

4-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 $663, price is now $419 per person
$419
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,359, price is now $861 per person
$861
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,165, price is now $1,444 per person
$1,444
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Westwinds Waterfront Resort

Westwinds Waterfront Resort

3 out of 5
Price was $845, price is now $589 per person
$589
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Price was $832, price is now $588 per person
$588
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,130, price is now $800 per person
$800
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,169, price is now $833 per person
$833
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,242, price is now $886 per person
$886
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

4 out of 5
Save 100% on your flight
Price was $1,134, price is now $810 per person
$810
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Sunrise Garden Resort

Sunrise Garden Resort

2 out of 5
Price was $1,010, price is now $724 per person
$724
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3.5 out of 5
Save 100% on your flight
Price was $1,080, price is now $777 per person
$777
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Hartford (BDL) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Price was $1,402, price is now $1,016 per person
$1,016
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)

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 $813, price is now $550 per person
$550
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Cottages at Siesta Key Inn

Cottages at Siesta Key Inn

3 out of 5
Save 100% on your flight
Price was $1,251, price is now $871 per person
$871
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip flight included
Des Moines (DSM) to Tampa (TPA)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $3,633, price is now $2,269 per person
$2,269
per person
Nov 22 - Nov 27
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 $1,755, price is now $1,103 per person
$1,103
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Siesta Palms By the Beach

Siesta Palms By the Beach

3.5 out of 5
Save 100% on your flight
Price was $1,430, price is now $921 per person
$921
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Siesta Key Inn

Siesta Key Inn

2 out of 5
Save 100% on your flight
Price was $1,288, price is now $832 per person
$832
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,379, price is now $899 per person
$899
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

4 out of 5
Save 100% on your flight
Price was $4,091, price is now $2,690 per person
$2,690
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Azul Resort

Azul Resort

2 out of 5
Save 100% on your flight
Price was $1,222, price is now $807 per person
$807
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Save 100% on your flight
Price was $1,087, price is now $722 per person
$722
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,203, price is now $803 per person
$803
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
St. Louis (STL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,347, price is now $918 per person
$918
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

6-7 night Longboat Key vacations

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

Carlisle Inn

3.5 out of 5
Price was $931, price is now $680 per person
$680
per person
Dec 10 - Dec 16
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 $1,750, price is now $1,068 per person
$1,068
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
The Knickerbocker by Delphius

The Knickerbocker by Delphius

3 out of 5
Save 100% on your flight
Price was $1,970, price is now $1,242 per person
$1,242
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Siesta Key Inn

Siesta Key Inn

2 out of 5
Save 100% on your flight
Price was $1,996, price is now $1,313 per person
$1,313
per person
Nov 26 - Dec 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

4 out of 5
Save 100% on your flight
Price was $2,086, price is now $1,401 per person
$1,401
per person
Nov 26 - Dec 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,444, price is now $972 per person
$972
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip 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 $1,194, price is now $807 per person
$807
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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 $1,104, price is now $748 per person
$748
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3.5 out of 5
Save 100% on your flight
Price was $1,916, price is now $1,300 per person
$1,300
per person
Nov 26 - Dec 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $1,298, price is now $954 per person
$954
per person
Nov 26 - Dec 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $1,243, price is now $923 per person
$923
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Siesta Palms By the Beach

Siesta Palms By the Beach

3.5 out of 5
Save 100% on your flight
Price was $1,666, price is now $1,242 per person
$1,242
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)

Flight deals to Longboat Key

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Feb 1 - Fri, Feb 5
BOS
Boston
SRQ
Sarasota
$150 Roundtrip, found 1 day ago
$150
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Mon, Feb 1 from Boston to Sarasota, returning Fri, Feb 5, priced at $150 found 1 day ago
Thu, Oct 29 - Sun, Nov 1
LGA
New York
SRQ
Sarasota
$287 Roundtrip, found 2 days ago
$287
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Oct 29 from New York to Sarasota, returning Sun, Nov 1, priced at $287 found 2 days ago
Wed, Dec 16 - Tue, Dec 22
ATL
Atlanta
SRQ
Sarasota
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Dec 16 from Atlanta to Sarasota, returning Tue, Dec 22, priced at $299 found 1 day ago

Top rated hotels for your Longboat Key vacation

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
$259 nightly
The price is $293 total per night
$293 total
Oct 18 - Oct 19
Total with taxes and fees
When you stay at Zota Beach Resort in Longboat Key, you'll be on the beach, within a 10-minute drive of Bradenton Beach and Coquina Beach.
On private beach
Pool
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
5.05 mi from city center
$854 nightly
The price is $965 total per night
$965 total
Oct 20 - Oct 21
Total with taxes and fees
When you stay at The St. Regis Longboat Key Resort in Longboat Key, you'll be on the beach, within a 15-minute drive of Lido Beach and St. Armands Circle.
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
Oct 20 - Oct 21
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 St. Armands Circle.
On private beach
Pool
Don't see what you're looking for?
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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.

Top Picks

^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.