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3-night Longboat Key vacations

Prices and availability subject to change. Additional terms may apply.
The Avalon Club

The Avalon Club

4 out of 5
per person
Jun 1 - Jun 4
Roundtrip flight included
Chicago (MDW) 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 1 - Jun 4
Roundtrip flight included
Chicago (MDW) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
May 31 - Jun 3
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
May 31 - Jun 3
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
May 31 - Jun 3
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
May 31 - Jun 3
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Nordvind Resort

Nordvind Resort

3 out of 5
Save 100% on your flight
per person
May 31 - Jun 3
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
May 31 - Jun 3
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Sheraton Sand Key Resort

Sheraton Sand Key Resort

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 4
Roundtrip flight included
Chicago (MDW) to Tampa (TPA)
Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 4
Roundtrip flight included
Chicago (MDW) to Tampa (TPA)
La Tortuga

La Tortuga

2.5 out of 5
Save 100% on your flight
per person
May 31 - Jun 3
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Clearwater Beach Hotel

Clearwater Beach Hotel

2 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 4
Roundtrip flight included
Chicago (MDW) to Tampa (TPA)

4-night Longboat Key vacations

Prices and availability subject to change. Additional terms may apply.
The Avalon Club

The Avalon Club

4 out of 5
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 17
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
May 31 - Jun 4
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) 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
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) 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
May 31 - Jun 4
Roundtrip flight included
Cleveland (CLE) 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
May 31 - Jun 4
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 17
Roundtrip flight included
Cleveland (CLE) 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
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)

5-night Longboat Key vacations

Prices and availability subject to change. Additional terms may apply.
The Avalon Club

The Avalon Club

4 out of 5
per person
Jun 8 - Jun 13
Roundtrip non-stop flight included
Chicago (CHI) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 20
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 20
Roundtrip flight included
Detroit (DTW) 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 8 - Jun 13
Roundtrip non-stop flight included
Chicago (CHI) 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
May 26 - May 31
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
per person
May 26 - May 31
Roundtrip flight included
Detroit (DTW) 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
May 26 - May 31
Roundtrip flight included
Detroit (DTW) 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 1 - Jun 6
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
Treasure Bay Resort & Marina

Treasure Bay Resort & Marina

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 20
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 20
Roundtrip flight included
Chicago (CHI) to Tampa (TPA)
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
May 26 - May 31
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)

6-7 night Longboat Key vacations

Prices and availability subject to change. Additional terms may apply.
The Avalon Club

The Avalon Club

4 out of 5
per person
May 26 - Jun 2
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 15
Roundtrip flight included
Philadelphia (PHL) 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 9 - Jun 15
Roundtrip 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 9 - Jun 15
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 9 - Jun 15
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 2
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 15
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 2
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
May 25 - May 31
Roundtrip non-stop flight included
Philadelphia (PHL) to Sarasota (SRQ)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 2
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 15
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Treasure Bay Resort & Marina

Treasure Bay Resort & Marina

3 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 15
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)

Flight deals to Longboat Key

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

Tue, Jun 11 - Tue, Jun 25
PHL
Philadelphia
SRQ
Sarasota
$71 Roundtrip, found 1 day ago
$71
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jun 11 from Philadelphia to Sarasota, returning Tue, Jun 25, priced at $71 found 1 day ago
Fri, May 10 - Sun, May 12
BOS
Boston
SRQ
Sarasota
$128 Roundtrip, found 13 hours ago
$128
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Fri, May 10 from Boston to Sarasota, returning Sun, May 12, priced at $128 found 13 hours ago
Sun, Jun 2 - Thu, Jun 13
JFK
New York
SRQ
Sarasota
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Jun 2 from New York to Sarasota, returning Thu, Jun 13, priced at $202 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 $274 per night
$274
per night
May 22 - May 23
When you stay at Zota Beach Resort in Longboat Key, you'll be on the waterfront, within a 10-minute drive of Coquina Beach and Cortez 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 $440 per night
$440
per night
May 13 - May 14
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.
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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.