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.
La Quinta Inn & Suites by Wyndham USF (Near Busch Gardens)

La Quinta Inn & Suites by Wyndham USF (Near Busch Gardens)

2.5 out of 5
per person
Jan 9 - Jan 12
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
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Beach House Suites by the Don CeSar

Beach House Suites by the Don CeSar

3 out of 5
Save 100% on your flight
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
The Hemingway

The Hemingway

4 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Silver Sands

Silver Sands

3.5 out of 5
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
The Saint Hotel

The Saint Hotel

2 out of 5
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Legacy Vacation Resorts - Indian Shores

Legacy Vacation Resorts - Indian Shores

3 out of 5
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Sheraton Sand Key Resort

Sheraton Sand Key Resort

4 out of 5
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)

4-night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jan 5 - Jan 9
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
per person
Jan 2 - Jan 6
found 23 hours ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
per person
Jan 2 - Jan 6
found 23 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

2 out of 5
per person
Jan 2 - Jan 6
found 23 hours ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
The Saint Hotel

The Saint Hotel

2 out of 5
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Hyatt Regency Sarasota

Hyatt Regency Sarasota

4 out of 5
Save 100% on your flight
per person
Jan 4 - Jan 8
just found
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
per person
Jan 2 - Jan 6
found 23 hours ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Aloft Tampa Midtown

Aloft Tampa Midtown

3 out of 5
Save 100% on your flight
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

3.5 out of 5
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)

5-night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jan 14 - Jan 19
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 3 hours ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Hampton Inn & Suites Tampa Riverview Brandon

Hampton Inn & Suites Tampa Riverview Brandon

2.5 out of 5
Save 100% on your flight
per person
Jan 15 - Jan 20
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
per person
Dec 25 - Dec 30
found 3 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
The Pointe Condos by Barsala

The Pointe Condos by Barsala

4.5 out of 5
Save 100% on your flight
per person
Jan 15 - Jan 20
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
per person
Dec 25 - Dec 30
found 3 hours ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Fanta-Sea on the Beach by Beachside Management - 49 Beach Rd

Fanta-Sea on the Beach by Beachside Management - 49 Beach Rd

4 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 3 hours ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
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
per person
Jan 13 - Jan 18
found 22 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jan 13 - Jan 18
found 22 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
per person
Dec 25 - Dec 30
found 3 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)

6-7 night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
Save 100% on your flight
per person
Jan 1 - Jan 7
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
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Save 100% on your flight
per person
Jan 1 - Jan 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

3.5 out of 5
Save 100% on your flight
per person
Jan 2 - Jan 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Element Tampa Midtown

Element Tampa Midtown

3 out of 5
Save 100% on your flight
per person
Jan 1 - Jan 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jan 2 - Jan 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Legacy Vacation Resorts - Indian Shores

Legacy Vacation Resorts - Indian Shores

3 out of 5
Save 100% on your flight
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Holiday Inn Tampa North, an IHG Hotel

Holiday Inn Tampa North, an IHG Hotel

3 out of 5
Save 100% on your flight
per person
Jan 1 - Jan 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Aloft Tampa Midtown

Aloft Tampa Midtown

3 out of 5
Save 100% on your flight
per person
Jan 1 - Jan 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Save 100% on your flight
per person
Jan 1 - Jan 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)

Flight deals to Longboat Key

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

Sat, Dec 14 - Tue, Dec 17
PHL
Philadelphia
SRQ
Sarasota
$68 Roundtrip, found 13 hours ago
$68
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, Dec 14 from Philadelphia to Sarasota, returning Tue, Dec 17, priced at $68 found 13 hours ago
Fri, Jan 10 - Mon, Jan 13
ORD
Chicago
SRQ
Sarasota
$126 Roundtrip, found 1 day ago
$126
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jan 10 from Chicago to Sarasota, returning Mon, Jan 13, priced at $126 found 1 day ago
Mon, Feb 10 - Tue, Feb 18
BOS
Boston
SRQ
Sarasota
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Feb 10 from Boston to Sarasota, returning Tue, Feb 18, priced at $137 found 3 days 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
The price is $925 per night
$925
includes taxes & fees
$819 per night
Dec 15 - Dec 16
When you stay at The St. Regis Longboat Key Resort in Longboat Key, you'll be on the waterfront, within a 10-minute drive of Lido Beach and St. Armands Circle.
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
The price is $302 per night
$302
includes taxes & fees
$270 per night
Dec 8 - Dec 9
When you stay at Zota Beach Resort in Longboat Key, you'll be on the waterfront, 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
The price is $471 per night
$471
includes taxes & fees
$417 per night
Dec 2 - Dec 3
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
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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.