Cheap Vacations in Longboat Key

Choose two or more items and save on your trip:

3-night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
Seffner Inn and Suites

Seffner Inn and Suites

2.5 out of 5
Price was $416, price is now $306 per person
$306
per person
Mar 1 - Mar 4
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,696, price is now $1,178 per person
$1,178
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,082, price is now $1,482 per person
$1,482
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,570, price is now $1,133 per person
$1,133
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Sarasota (SRQ)
DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
Price was $581, price is now $422 per person
$422
per person
Mar 1 - Mar 4
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sarasota (SRQ)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $997, price is now $731 per person
$731
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $666, price is now $492 per person
$492
per person
Mar 14 - Mar 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Cambria Hotel Tampa-Brandon

Cambria Hotel Tampa-Brandon

3 out of 5
Price was $504, price is now $375 per person
$375
per person
Mar 1 - Mar 4
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $1,097, price is now $821 per person
$821
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

3 out of 5
Price was $925, price is now $692 per person
$692
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $1,146, price is now $867 per person
$867
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sarasota (SRQ)
Ramada by Wyndham Venice Hotel Venezia

Ramada by Wyndham Venice Hotel Venezia

3.5 out of 5
Price was $769, price is now $584 per person
$584
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)

4-night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $570, price is now $338 per person
$338
per person
Feb 21 - Feb 25
found 11 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $971, price is now $560 per person
$560
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,397, price is now $861 per person
$861
per person
Mar 13 - Mar 17
found 19 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,150, price is now $711 per person
$711
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
Save 100% on your flight
Price was $988, price is now $664 per person
$664
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Austin (AUS) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $3,631, price is now $2,457 per person
$2,457
per person
Mar 13 - Mar 17
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,160, price is now $801 per person
$801
per person
Feb 23 - Feb 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Save 100% on your flight
Price was $2,408, price is now $1,680 per person
$1,680
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $1,082, price is now $761 per person
$761
per person
Mar 13 - Mar 17
found 19 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Tampa (TPA)
Landing Palmetto Apartments

Landing Palmetto Apartments

4 out of 5
Save 100% on your flight
Price was $1,060, price is now $746 per person
$746
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sarasota (SRQ)
Arvilla

Arvilla

2 out of 5
Save 100% on your flight
Price was $804, price is now $570 per person
$570
per person
Feb 23 - Feb 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,245, price is now $882 per person
$882
per person
Mar 13 - Mar 17
found 19 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Sarasota (SRQ)

5-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
Price was $984, price is now $650 per person
$650
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,424, price is now $887 per person
$887
per person
Mar 8 - Mar 13
found 7 hours ago
Roundtrip flight included
Denver (DEN) to Sarasota (SRQ)
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Price was $1,952, price is now $1,251 per person
$1,251
per person
Feb 25 - Mar 2
found 8 hours ago
Roundtrip flight included
San Juan (SJU) to Tampa (TPA)
Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

3 out of 5
Save 100% on your flight
Price was $1,108, price is now $744 per person
$744
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $1,069, price is now $718 per person
$718
per person
Mar 8 - Mar 13
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,644, price is now $1,123 per person
$1,123
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,480, price is now $1,020 per person
$1,020
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $1,385, price is now $956 per person
$956
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Price was $1,265, price is now $874 per person
$874
per person
Feb 25 - Mar 2
found 8 hours ago
Roundtrip flight included
San Juan (SJU) to Tampa (TPA)
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,485, price is now $1,026 per person
$1,026
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Residence Inn by Marriott Sarasota Bradenton

Residence Inn by Marriott Sarasota Bradenton

3 out of 5
Save 100% on your flight
Price was $1,175, price is now $816 per person
$816
per person
Mar 8 - Mar 13
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Fairfield Inn & Suites by Marriott Sarasota Lakewood Ranch

Fairfield Inn & Suites by Marriott Sarasota Lakewood Ranch

2.5 out of 5
Save 100% on your flight
Price was $1,225, price is now $852 per person
$852
per person
Mar 8 - Mar 13
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Sarasota (SRQ)

6-7 night Longboat Key vacations

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $1,048, price is now $638 per person
$638
per person
Feb 17 - Feb 24
found 1 hour ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,541, price is now $850 per person
$850
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
Price was $2,709, price is now $1,533 per person
$1,533
per person
Feb 21 - Feb 27
found 7 hours ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,695, price is now $993 per person
$993
per person
Mar 8 - Mar 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,262, price is now $757 per person
$757
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $2,049, price is now $1,237 per person
$1,237
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Save 100% on your flight
Price was $1,574, price is now $968 per person
$968
per person
Mar 8 - Mar 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
Save 100% on your flight
Price was $1,106, price is now $691 per person
$691
per person
Feb 17 - Feb 24
found 1 hour ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
Save 100% on your flight
Price was $1,518, price is now $956 per person
$956
per person
Mar 8 - Mar 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,473, price is now $1,580 per person
$1,580
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Sarasota (SRQ)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,497, price is now $965 per person
$965
per person
Feb 17 - Feb 23
found 1 day ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
Save 100% on your flight
Price was $1,622, price is now $1,047 per person
$1,047
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Sarasota (SRQ)

Flight deals to Longboat Key

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

Mon, Feb 2 - Tue, Feb 3
JFK
New York
SRQ
Sarasota
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Feb 2 from New York to Sarasota, returning Tue, Feb 3, priced at $157 found 1 day ago
Mon, Feb 2 - Tue, Feb 3
EWR
New York
SRQ
Sarasota
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select United flight, departing Mon, Feb 2 from New York to Sarasota, returning Tue, Feb 3, priced at $157 found 1 day ago
Fri, Jan 30 - Sat, Jan 31
LGA
New York
SRQ
Sarasota
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jan 30 from New York to Sarasota, returning Sat, Jan 31, priced at $177 found 1 day 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
5.05 mi from city center
$1,154 nightly
The price is $1,304 total per night
$1,304 total
Jan 19 - Jan 20
Total with taxes and fees
When you stay at The St. Regis Longboat Key Resort in Longboat Key, you'll be on the beach, within a 10-minute drive of St. Armands Circle and Lido Beach.
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
$269 nightly
The price is $304 total per night
$304 total
Jan 19 - Jan 20
Total with taxes and fees
When you stay at Zota Beach Resort in Longboat Key, you'll be on the beach, within a 10-minute drive of Bradenton 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
7.04 mi from city center
$549 nightly
The price is $620 total per night
$620 total
Jan 19 - Jan 20
Total with taxes and fees
When you stay at The Resort at Longboat Key Club in Longboat Key, you'll be by the ocean, a 4-minute drive from Mote Marine Laboratory & Aquarium and 5 minutes from St. Armands Circle.
On private beach
Pool
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.