Longboat Key Vacation Packages

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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.
Ramada by Wyndham Venice Hotel Venezia

Ramada by Wyndham Venice Hotel Venezia

3.5 out of 5
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Sarasota (SRQ)
7.2/10 Good! (1,008 reviews)
My husband and I stayed for 2 nights and we had to get our key cards replaced 3x! My daughter and family stayed in the suite and had ants in the bed. Pool was excellent

Reviewed on Aug. 1, 2025

GALAXY HOTEL

GALAXY HOTEL

3.5 out of 5
Downtown St. Petersburg
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8/10 Very Good! (238 reviews)
Great Location , Clean Rooms, and spacious.

Reviewed on Aug. 1, 2025

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
per person
Oct 17 - Oct 23
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (4,087 reviews)
I spent 2 nights here with my best friend for a birthday getaway and it exceeded our expectations. Every aspect of our stay was a 10 +! The front desk & housekeeping were all smiles at every interaction! Would most definitely recommend and I would stay there again if I am back in the area.

Reviewed on Jul. 30, 2025

Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (1,009 reviews)
The room is clean. The property is in good location

Reviewed on Jul. 30, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (557 reviews)
A very clean hotel. Well worth the money for that fact alone.

Reviewed on Jul. 28, 2025

Ready to book your vacation to Longboat Key?

 

Choose your dates

Longboat Key Hotel Deals

The St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

5 out of 5
1601 Gulf Of Mexico Drive, Longboat Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $964 per night from Aug 19 to Aug 20
CA $964
CA $1,175 total
Aug 19 - Aug 20
includes taxes & fees
9.6/10 Exceptional! (34 reviews)
"Amazing"

Reviewed on Jul. 22, 2025

The St. Regis Longboat Key Resort
Zota Beach Resort

Zota Beach Resort

4 out of 5
4711 Gulf of Mexico Dr, Longboat Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $343 per night from Sep 2 to Sep 3
CA $343
CA $450 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Live it!"

Reviewed on Jul. 27, 2025

Zota Beach Resort
The Resort at Longboat Key Club

The Resort at Longboat Key Club

4 out of 5
220 Sands Point Road, Longboat Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $556 per night from Sep 1 to Sep 2
CA $556
CA $691 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (660 reviews)
"/"

Reviewed on Jul. 31, 2025

The Resort at Longboat Key Club
See all 844 properties in Longboat Key
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Longboat Key

Robinson Preserve Mangrove Tour

Robinson Preserve Mangrove Tour

CA $75
per adult
Robinson Preserve Mangrove Tour
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

CA $89
per adult
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
Picture 4 for Activity Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

CA $75
per adult
100% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
See all activities in Longboat Key

Frequently asked questions

How much does a Longboat Key vacation package cost?
You'll find cheap prices from CA $512 on Expedia for your Longboat Key getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Longboat Key costs.
What are the cheapest months to go to Longboat Key?
If you'd like to book a cheap Longboat Key vacation package, consider planning a trip in January, August and December. You'll usually find lower rates on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for Longboat Key?
To get the most out of a Longboat Key vacation, we suggest booking for 3 days. Split your time between discovering Jewfish Key, Anna Maria Sound and other must-see attractions, in addition to exploring neighbourhoods like Bayshore Gardens and South Bradenton. If you've got some time to spare, include a day trip or tour in your Longboat Key vacation itinerary.
Is it worth booking a vacation package to Longboat Key?
Longboat Key has all the ingredients you need for a fantastic break — coastal beaches, views and watersports are just the start. Whether you want to visit attractions like Jewfish Key and Cannons Marina, or take the path less travelled, there's plenty to see and do on your Longboat Key vacation.
How to find the best Longboat Key package deals?
Bagging a cheap Longboat Key package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add some filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Longboat Key package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Longboat Key vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can personalize your Longboat Key trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Longboat Key?
If you're considering an impromptu Longboat Key vacation, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Longboat Key?

  1. Choose your dates: The things you plan to do in Longboat Key and your favourite season will help you decide when to get away.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and activities. Your accommodations will probably be the largest expense during your trip to Longboat Key.
  3. Decide how long to go for: Now that you're up to speed on Longboat Key, you can work out the ideal length of your vacation. Create a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Longboat Key vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.