
Longboat Key Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Longboat Key Vacation
With a reputation for its laid-back lifestyle and spectacular views, Longboat Key is an ideal getaway destination. Lock in one of our Longboat Key vacation packages and experience all that this fascinating city has to offer. IMG Academy, Coquina Beach and Cortez Beach are just a few of the attractions worth checking out during your trip to Longboat Key. Expedia will help you escape your daily routine. Tailor your vacation to Longboat Key to suit your travel style, whatever that may be.
Top Longboat Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.

ChartHouse Clearwater Beach Marina Hotel
Price was CA $1,662, price is now CA $1,072 per person
CA $1,072
per person
Jul 25 - Jul 31
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,005 reviews)
Overall, a good place for the vacation
Reviewed on May 15, 2026

The BC Resort on the Water
Price was CA $1,867, price is now CA $1,103 per person
CA $1,103
per person
Jun 29 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
7.8/10 Good! (18 reviews)
We had a great stay at this condo during our trip to Florida. Everything was very clean and well maintained, which made it easy to relax right away. Communication was excellent—clear, prompt, and the instructions were simple to follow from check-in to check-out. The accommodations were comfortable and nicely set up, with everything we needed for our stay. The location was a big highlight—perfect for easy beach access and close to plenty of activities. We would definitely stay here again.
Reviewed on Apr 24, 2026

Ocean Club Treasure Island Hotel
Sunshine Beach
Price was CA $3,176, price is now CA $1,882 per person
CA $1,882
per person
Jun 29 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (932 reviews)
Nice location
Easy check in and out
Great ocean view and walkable to beach
Nice pool
Easy to park vehicle on property
Some of the staff were super friendly.
Room was lovely but beds need to be replaced.
In room washer and dryer did not work properly.
Reviewed on May 17, 2026

Cedar Cove Resort and Cottages
Price was CA $2,532, price is now CA $1,588 per person
CA $1,588
per person
Jul 27 - Aug 3
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (506 reviews)
Property was great! I would definitely recommend people to stay here great place parking is a bit of an issue if you have more than one car coming in but that comes with the island pretty typical but overall great
Reviewed on May 17, 2026
Longboat Key Hotel Deals

Zota Beach Resort
4711 Gulf of Mexico Dr Longboat Key FL
Fully refundableReserve now, pay when you stay
The price is CA $342 per night from May 31 to Jun 1
CA $342
CA $449 total
May 31 - Jun 1
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
"A great place to stay with very convenient amenities. The pool area and beach access are very clean, accessible, and accommodating to all guests."
Reviewed on May 15, 2026

The St. Regis Longboat Key Resort
1601 Gulf Of Mexico Drive Longboat Key FL
Fully refundableReserve now, pay when you stay
The price is CA $1,236 per night from Jun 9 to Jun 10
CA $1,236
CA $1,498 total
Jun 9 - Jun 10
includes taxes & fees
9.8/10 Exceptional! (73 reviews)
"Lovely new five star resort, great room designs w ocean views and great pools. Only issue was getting reservations at the steak restaurant so make sure you book before you arrive."
Reviewed on May 14, 2026

The Resort at Longboat Key Club
220 Sands Point Road Longboat Key FL
Fully refundableReserve now, pay when you stay
The price is CA $659 per night from May 26 to May 27
CA $659
CA $822 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (708 reviews)
"I received a pedicure while a guest there. My pedicurist was a lot of fun. I relaxed, & we laughed a lot. SHe was professional, positive, and fun. The pedicure was pretty good, but the experience was excellent."
Reviewed on Apr 30, 2026
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.
What to do in Longboat Key

Mangrove Tunnel & Manatee Kayak Eco-Tour
CA $81
per adult
94% of travellers recommend

Sarasota Guided Mangrove Tunnel Kayak Tour
CA $81
per adult
96% of travellers recommend

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
CA $75
per adult
98% of travellers recommend
Explore a world of travel with Expedia
- 1 Star Hotels in Sunny Shores
- Family Hotels in Bay Isles
- Oceanfront Hotels in Bay Isles
- Bay Isles Hotels
- Adults Only Resorts & in Bayshore Gardens
- Cheap Hotels in Bayshore Gardens
- Hotels with Early Check-in in Bayshore Gardens
- Lgbt Friendly Hotels in Bayshore Gardens
- Mountain Hotels in Bayshore Gardens
- Oceanfront Hotels in Bayshore Gardens
- Bayshore Gardens Hotels
- Condo Rentals in Bradenton Beach
- Adults Only Resorts & in Bradenton Beach
- Beach Hotel Hotels in Bradenton Beach
- Hotels with a Lazy River in Bradenton Beach
- La Quinta Inn & Suites Hotels in Bradenton Beach
- Oceanfront Hotels in Bradenton Beach
- Bradenton Beach Hotels
- Vacation Homes in Bradenton Beach
- Resorts in Bradenton Beach
- Hotels near Coquina Beach
- Adults Only Resorts & in Coral Shores
- Beach Hotel Hotels in Coral Shores
- Golf Hotels in Coral Shores
- Mountain Hotels in Coral Shores
- Spa Hotels in Coral Shores
- Coral Shores Hotels
- Aparthotels in Cortez
- Hotels near Cortez Beach
- B&B in Cortez
- Cabin Rentals in Cortez
- Castles in Cortez
- Condo Rentals in Cortez
- Guest Houses in Cortez
- Beach Hotel Hotels in Cortez
- Cheap Hotels in Cortez
- Luxury Hotels in Cortez
- Pet-Friendly Hotels in Cortez
- Cortez Hotels
- Inns in Cortez
- Motels in Cortez
- Resorts in Cortez
- Townhomes in Cortez
- Hotels near Historic Bridge Street Pier
- Hotels near IMG Academy
- Hotels near IMG Bollettieri Tennis Academy
- Hotels near IMG Soccer Academy
- Adults Only Resorts & in Longbeach Village
- All Inclusive Resorts and in Longbeach Village
- Lgbt Friendly Hotels in Longbeach Village
- Oceanfront Hotels in Longbeach Village
- Longbeach Village Hotels
- Hotels near Longboat Key Beaches
- Adults Only Resorts & in Sunny Shores
- All Inclusive Resorts and in Sunny Shores
- Beach Hotel Hotels in Sunny Shores
- Casino Hotels in Sunny Shores
- Cheap Hotels in Sunny Shores
- Hotels & Resorts for Couples in Sunny Shores
- Honeymoon Resorts and in Sunny Shores
- Hotels with Early Check-in in Sunny Shores
- Mountain Hotels in Sunny Shores
- Waterpark Hotels in Sunny Shores
- Sunny Shores Hotels
- Anna Maria Island Vacations
- Anna Maria Vacations
- Bean Point Beach
- Visit Bayshore Gardens
- Bradenton Beach
- Bradenton Beach Vacations
- Bradenton Vacations
- Ca’ d’Zan
- Coquina Baywalk
- Cortez Beach
- Ed Smith Stadium
- Historic Bridge Street Pier
- Holmes Beach Vacations
- Img Academy
- Img Bollettieri Tennis Academy
- John and Mable Ringling Museum of Art
- Lido Beach
- Lido Key Vacations
- Visit Longbeach Village
- Marie Selby Botanical Gardens
- Mote Marine Laboratory & Aquarium
- Powel Crosley Estate
- Red Barn Flea Market Plaza
- Sarasota BayWalk
- Sarasota Classic Car Museum
- Sarasota Jungle Gardens
- Sarasota Opera House
- Sarasota Vacations
- Siesta Key Vacations
- St. Armands Circle
- The Bishop Museum of Science and Nature
- Van Wezel Performing Arts Hall
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.








