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.
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 20
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
per person
Jul 2 - Jul 5
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 6
Roundtrip non-stop flight included
Pittsburgh (PIT) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 20
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
Jun 24 - Jun 27
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 5
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
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
Jun 14 - Jun 17
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
Jun 17 - Jun 20
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 5
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

4-night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
Clearwater Beach Hotel

Clearwater Beach Hotel

2 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 21
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
per person
Jun 17 - Jun 21
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 21
Roundtrip non-stop flight included
Philadelphia (PHL) 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
Jun 19 - Jun 23
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
per person
Jun 24 - Jun 28
Roundtrip non-stop flight included
Richmond (RIC) to Tampa (TPA)
The Capri at Siesta

The Capri at Siesta

3 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 2
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 28
Roundtrip non-stop flight included
Richmond (RIC) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 28
Roundtrip non-stop flight included
Richmond (RIC) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 2
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 17
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
FUSION Resort Two Bedroom Suites

FUSION Resort Two Bedroom Suites

3.5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 28
Roundtrip non-stop flight included
Richmond (RIC) to Tampa (TPA)

5-night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
Tortuga Inn Beach Resort

Tortuga Inn Beach Resort

2.5 out of 5
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

2 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
The Retreat at Anna Maria Island Inn

The Retreat at Anna Maria Island Inn

2 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) 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
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Cottage Haven-one Minute Walk To The Beach-private Yards-keyless Locks

Cottage Haven-one Minute Walk To The Beach-private Yards-keyless Locks

3.5 out of 5
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Tradewinds Beach Resort

Tradewinds Beach Resort

2.5 out of 5
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Cottage Haven-one Minute Walk To The Beach-private Yards-keyless Locks

Cottage Haven-one Minute Walk To The Beach-private Yards-keyless Locks

2 out of 5
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)

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
per person
Jun 16 - Jun 22
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 23 - Jun 29
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
Jun 16 - Jun 22
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 22
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jun 23 - Jun 29
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
Save 100% on your flight
per person
Jun 23 - Jun 29
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Sirata Beach Resort

Sirata Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 23 - Jun 29
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Sailport Waterfront Suites

Sailport Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 22
Roundtrip flight included
Chicago (ORD) 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
per person
Jun 16 - Jun 22
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Barefoot Beach Club

Barefoot Beach Club

2.5 out of 5
Save 100% on your flight
per person
Jun 23 - Jun 29
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
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
Jun 16 - Jun 22
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
per person
Jun 16 - Jun 22
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

Flight deals to Longboat Key

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

Sun, Jul 28 - Thu, Aug 15
PHL
Philadelphia
SRQ
Sarasota
$88 Roundtrip, found 6 days ago
$88
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Jul 28 from Philadelphia to Sarasota, returning Thu, Aug 15, priced at $88 found 6 days ago
Tue, Aug 27 - Wed, Sep 11
JFK
New York
SRQ
Sarasota
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Aug 27 from New York to Sarasota, returning Wed, Sep 11, priced at $147 found 2 days ago
Thu, May 30 - Sat, Jun 15
ORD
Chicago
SRQ
Sarasota
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 30 from Chicago to Sarasota, returning Sat, Jun 15, priced at $155 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
The price is $239 per night
$239
per night
Jun 13 - Jun 14
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 St. Armands Circle.
Pool
On private beach
The Resort at Longboat Key Club

The Resort at Longboat Key Club

4 out of 5
220 Sands Point Road, Longboat Key, FL
6.89 mi from city center
The price is $399 per night
$399
per night
Jun 10 - Jun 11
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.
Sea Club I Beach Resort

Sea Club I Beach Resort

3 out of 5
4141 Gulf of Mexico Drive, Longboat Key, FL
1.89 mi from city center
Get rates
When you stay at Sea Club I Beach Resort in Longboat Key, you'll be on the beach, within a 10-minute drive of Coquina Beach and Mote Marine Laboratory & Aquarium.
Pool
Parking included
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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.