Cheap Vacations in Longboat Key

Choose two or more items and save on your trip:

3-night Longboat Key vacations

Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
May 23 - May 26
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
May 30 - Jun 2
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
May 24 - May 27
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
May 24 - May 27
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
May 26 - May 29
Roundtrip flight included
Newark (EWR) to Sarasota (SRQ)
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 24 - May 27
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 29 - Jun 1
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
May 29 - Jun 1
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
May 29 - Jun 1
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip non-stop 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
May 29 - Jun 1
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
Nordvind Resort

Nordvind Resort

3 out of 5
Save 100% on your flight
per person
May 29 - Jun 1
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
Prices and availability subject to change. Additional terms may apply.

4-night Longboat Key vacations

Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 4 - Jun 8
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
May 24 - May 28
Roundtrip non-stop flight included
Columbus (CMH) 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 23 - May 27
Roundtrip non-stop 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
May 24 - May 28
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 10 - Jun 14
Roundtrip flight included
Denver (DEN) 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 24 - May 28
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jun 4 - Jun 8
Roundtrip non-stop 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
Jun 4 - Jun 8
Roundtrip non-stop flight included
Chicago (ORD) 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 10 - Jun 14
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Treasure Bay Resort & Marina

Treasure Bay Resort & Marina

3 out of 5
Save 100% on your flight
per person
Jun 4 - Jun 8
Roundtrip non-stop 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 4 - Jun 8
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
Jun 4 - Jun 8
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Prices and availability subject to change. Additional terms may apply.

5-night Longboat Key vacations

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 14
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 4 - Jun 9
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 10
Roundtrip flight included
Philadelphia (PHL) 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 5 - Jun 10
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 14
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 12 - Jun 17
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Treasure Bay Resort & Marina

Treasure Bay Resort & Marina

3 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 10
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
Jun 9 - Jun 14
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
Jun 12 - Jun 17
Roundtrip non-stop flight included
Newark (EWR) 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 5 - Jun 10
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 12 - Jun 17
Roundtrip non-stop flight included
Newark (EWR) 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 5 - Jun 10
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Prices and availability subject to change. Additional terms may apply.

6-7 night Longboat Key vacations

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 8
Roundtrip non-stop flight included
Columbus (CMH) 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 8
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 8
Roundtrip non-stop flight included
Columbus (CMH) 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 1 - Jun 8
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 8
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Barefoot Beach Club

Barefoot Beach Club

2.5 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 8
Roundtrip non-stop flight included
Columbus (CMH) 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 8
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Pelican Pointe Hotel by Sunsational Beach Rentals

Pelican Pointe Hotel by Sunsational Beach Rentals

2.5 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 8
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
The Cottages at Siesta Key

The Cottages at Siesta Key

2.5 out of 5
Save 100% on your flight
per person
May 23 - May 29
Roundtrip non-stop flight included
Philadelphia (PHL) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 8
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 8
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Turtle Beach Resort and Inn

Turtle Beach Resort and Inn

3.5 out of 5
Save 100% on your flight
per person
May 23 - May 29
Roundtrip non-stop flight included
Philadelphia (PHL) to Sarasota (SRQ)
Prices and availability subject to change. Additional terms may apply.

Flight deals to Longboat Key

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

Mon, May 6 - Thu, May 9
PHL
Philadelphia
SRQ
Sarasota
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, May 6 from Philadelphia to Sarasota, returning Thu, May 9, priced at $68 found 6 days ago
Mon, Apr 29 - Sun, May 12
BOS
Boston
SRQ
Sarasota
$117 Roundtrip, found 6 days ago
$117
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Apr 29 from Boston to Sarasota, returning Sun, May 12, priced at $117 found 6 days ago
Tue, May 21 - Fri, May 24
JFK
New York
SRQ
Sarasota
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, May 21 from New York to Sarasota, returning Fri, May 24, priced at $197 found 3 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 $304 per night
$304
per night
Apr 30 - May 1
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 $485 per night
$485
per night
Apr 21 - Apr 22
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.
Don't see what you're looking for?
See all available properties in Longboat Key
View all properties
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.