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.
Clearwater Beach Hotel

Clearwater Beach Hotel

2 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 27
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
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
Jul 4 - Jul 7
Roundtrip flight included
Newark (EWR) to Tampa (TPA)
Hotel Haya

Hotel Haya

4 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 27
Roundtrip flight included
Dallas (DFW) 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 21 - Jun 24
Roundtrip flight included
Dallas (DFW) to Sarasota (SRQ)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
per person
Jul 4 - Jul 7
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
Jul 11 - Jul 14
Roundtrip flight included
Newark (EWR) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
per person
Jul 4 - Jul 7
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Postcard Inn On The Beach

Postcard Inn On The Beach

3 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
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
Jul 4 - Jul 7
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 24 - Jun 27
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 12
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)

4-night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
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 21 - Jun 25
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 24
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 21 - Jun 25
Roundtrip flight included
Dallas (DFW) 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 21 - Jun 25
Roundtrip flight included
Dallas (DFW) 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 20 - Jun 24
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Sirata Beach Resort

Sirata Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 24
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 24
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
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per person
Jul 3 - Jul 7
Roundtrip flight included
Newark (EWR) 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 20 - Jun 24
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 24
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
per person
Jul 8 - Jul 12
Roundtrip flight included
Dallas (DFW) to Sarasota (SRQ)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 24
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)

5-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
Jun 26 - Jul 1
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 14
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 14
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
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
Jul 9 - Jul 14
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
Jul 9 - Jul 14
Roundtrip flight included
Chicago (ORD) 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
Jul 9 - Jul 14
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Pasa Tiempo Private Waterfront Resort - Adults Only

Pasa Tiempo Private Waterfront Resort - Adults Only

2 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 14
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
Jun 16 - Jun 21
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 22
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 22
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 25
Roundtrip non-stop flight included
Newark (EWR) 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 20 - Jun 25
Roundtrip non-stop flight included
Newark (EWR) 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
per person
Jun 25 - Jul 1
Roundtrip non-stop flight included
Dallas (DAL) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 25 - Jul 1
Roundtrip non-stop flight included
Dallas (DAL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 13
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 25 - Jul 1
Roundtrip non-stop flight included
Dallas (DAL) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jun 25 - Jul 1
Roundtrip non-stop flight included
Dallas (DAL) to Tampa (TPA)
Silver Sands

Silver Sands

3.5 out of 5
Save 100% on your flight
per person
Jun 25 - Jul 1
Roundtrip non-stop flight included
Dallas (DAL) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Save 100% on your flight
per person
Jul 8 - Jul 14
Roundtrip flight included
Chicago (ORD) 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 25 - Jul 1
Roundtrip non-stop flight included
Dallas (DAL) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
Jun 25 - Jul 1
Roundtrip non-stop flight included
Dallas (DAL) 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 25 - Jul 1
Roundtrip non-stop flight included
Dallas (DAL) to Tampa (TPA)
Treasure Bay Resort & Marina

Treasure Bay Resort & Marina

3 out of 5
Save 100% on your flight
per person
Jun 23 - Jun 29
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 23 - Jun 29
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.

Sat, Jun 8 - Tue, Jun 11
PHL
Philadelphia
SRQ
Sarasota
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jun 8 from Philadelphia to Sarasota, returning Tue, Jun 11, priced at $68 found 1 day ago
Sat, Jun 8 - Tue, Jun 11
MDW
Chicago
SRQ
Sarasota
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jun 8 from Chicago to Sarasota, returning Tue, Jun 11, priced at $139 found 2 days ago
Tue, Aug 27 - Wed, Sep 11
JFK
New York
SRQ
Sarasota
$147 Roundtrip, found 5 days ago
$147
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Aug 27 from New York to Sarasota, returning Wed, Sep 11, priced at $147 found 5 days 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.
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 $414 per night
$414
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.