A coastal road with a beach on one side and a marina with boats on the other.

Summerland Key Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Summerland Key Vacation

The hassle-free way to experience this interesting city is with a tailor-made Summerland Key vacation package. Base yourself in the neighborhood of Sugarloaf Shores, which is great for families, fishing and views or go someplace else — our package deals are all about you. Cook Island, Big Pine Key Flea Market and Blue Hole are just some of the sights you'll want to see during your trip to Summerland Key. Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Summerland Key vacation plans in motion!

Top Summerland Key vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Room
    Jan 10 - Jan 16

    Private Oasis at Arya + Flight

    Coconut Grove
    6 nights
    3.5 star property
    8.6/10 - Excellent (1,078 reviews)
    Roundtrip • Toronto (YTO) - Miami (MIA)
    YYZ - FLL • Nonstop FLL - YYZ • Nonstop
    CA $2,491
    CA $1,398
    per traveller
    found 1 day ago
    Private Oasis at Arya
  • A poolside area with lounge chairs, a table with a beverage, and a view of the ocean.
    Feb 1 - Feb 4

    The Retreat Collection at 1 Hotel & Homes South Beach + Flight

    South Beach
    3 nights
    5.0 star property
    8.0/10 - Very good (1 review)
    "Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay...."
    Reviewed June 22, 2016
    Roundtrip • Montreal (YUL) - Miami (MIA)
    YUL - FLL • 1 stop FLL - YUL • 1 stop
    CA $15,066
    CA $7,188
    per traveller
    found 18 hours ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • A beachside terrace with white rocking chairs and a white balustrade overlooking the ocean.
    Jan 24 - Jan 30

    Pelican Grand Beach Resort - A Noble House Resort + Flight

    East Fort Lauderdale
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,804 reviews)
    Roundtrip • Montreal (YMQ) - Miami (MIA)
    YUL - FLL • 1 stop FLL - YUL • 1 stop
    CA $3,880
    CA $2,136
    per traveller
    found 1 day ago
    Pelican Grand Beach Resort - A Noble House Resort
  • A pool area with a view of the ocean, American and Bentley flags, and potted plants.
    Jan 26 - Jan 29

    Bentley Hotel South Beach + Flight

    South Beach
    3 nights
    4.0 star property
    9.4/10 - Exceptional (1,249 reviews)
    "This Hotel, with it’s amazing Staff, went above and beyond. Nothing was too much trouble, organising Taxis and storing our luggage. The pool was amazing with views of South Beach"
    Reviewed November 6, 2026
    Roundtrip • Hamilton (YHM) - Miami (MIA)
    YHM - FLL • 1 stop FLL - YHM • 1 stop
    Save 100% on your flight
    CA $3,279
    CA $1,881
    per traveller
    found 21 hours ago
    Bentley Hotel South Beach
  • A balcony with two chairs and a small table, overlooking a pool and beach area with palm trees and a clear blue sky.
    Jan 17 - Jan 23

    Hotel Riu Plaza Miami Beach + Flight

    Mid Beach
    6 nights
    4.0 star property
    8.2/10 - Very good (1,235 reviews)
    "El cuarto estuvo muy bueno"
    Reviewed November 5, 2026
    Roundtrip • Hamilton (YHM) - Miami (MIA)
    YHM - MIA • 1 stop MIA - YHM • 1 stop
    CA $2,852
    CA $1,649
    per traveller
    found 1 day ago
    Hotel Riu Plaza Miami Beach

Where to stay in Summerland Key

Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. Learn more about Summerland Key
Learn more about Summerland Key
An aerial view of a long bridge over turquoise waters with a few vehicles on it.

Bay Point

Bay Point might not have many top sights, but Lower Sugarloaf Sound and Florida Keys Beaches are two attractions nearby that you can check out.
A calm lake with several white birds, including herons and pelicans, on the water's edge.

Cutthroat Harbor Estates

Cutthroat Harbour Estates offers a tranquil slice of Florida Keys living with private boat docks and crystal-clear waters. This residential waterfront area provides an authentic escape from tourist crowds. Homes on stilts with weathered wood docks create a classic Keys atmosphere. The neighborhood's canals connect directly to the Gulf, making it perfect for fishing and boating enthusiasts. Gentle waves lap against private docks while tropical birds call at dawn. Nearby Venture Out Keys and Summerland Key provide dining options and additional sights.
A waterfront property with a pool, palm trees, and a building with a white roof.

Sugarloaf Shores

Sugarloaf Shores offers a tranquil escape on the Florida Keys waterfront. Private homes line peaceful canals where turquoise waters invite fishing, kayaking, and boating adventures. This residential haven sits away from tourist crowds yet provides easy access to stunning ocean views. The neighborhood's charm lies in its authentic Keys lifestyle with homes on stilts and tropical landscaping. Nearby Sugarloaf Beach and Lower Sugarloaf Sound provide perfect spots for swimming and snorkelling. Visitors appreciate the quiet streets for evening strolls and stargazing.
An aerial view of a bridge over turquoise water.

Cudjoe Gardens

Cudjoe Gardens offers a peaceful waterfront retreat in the Florida Keys. This quiet residential haven features canal-front properties with private docks for easy boat access. Travellers can enjoy fishing, wildlife watching, and stargazing from their vacation rentals. The neighborhood's tropical charm comes alive with pastel homes on stilts surrounded by palm trees and native plants. A rental car is essential for exploring nearby Summerland Key attractions and dining options. Water enthusiasts will appreciate direct canal access to open waters and nearby beaches.
An aerial view of a coastal area with a long bridge connecting two landmasses, clear turquoise waters, and a clear blue sky with scattered clouds.

Breezeswept Beach Estates

Escape to the peaceful shores of Breezeswept Beach Estates on Summerland Key. This residential haven offers private waterfront properties with boat docks and direct access to crystal-clear Florida waters. The neighborhood's charm lies in its quiet streets lined with pastel homes and tropical landscaping. Outdoor enthusiasts will love exploring nearby Newfound Harbour Keys by kayak or boat. Fish in the shallow waters, spot native birds, or simply relax under swaying palms. With minimal commercialization and abundant natural beauty, this peaceful retreat captures authentic Keys living without the tourist crowds.

Discover the most popular places to visit in Summerland Key

Sugarloaf Beach

8.4/10 (38 reviews)
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
See properties

What to do in Summerland Key

Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $79
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
See all activities in Summerland Key

Summerland Key Hotel Deals

A waterfront building with a flat roof, large windows, and a balcony.

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
12.7 km from Summerland Key
8.2 out of 10, Very good, (1,000 reviews)
"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."
The price is CA $139
CA $156 total
includes taxes & fees
Nov 30 - Dec 1
Sugar Loaf Lodge
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.
See all properties in Summerland Key

Frequently Asked Questions

How much does a Summerland Key vacation package cost?

Offering great value package deals from CA $1,398 on Expedia, you'll be pleasantly surprised at how much a vacation to Summerland Key costs! Our packages make travel planning easier and your savings go further.

What are the cheapest months to go to Summerland Key?

If you're looking to book a cheap Summerland Key vacation package, consider travelling in September, October and November. You'll typically find better rates on hotels and airfares during these months — ideal for a budget-friendly break.

How many days is enough for Summerland Key?

We'd suggest booking a Summerland Key vacation for a minimum of 4 days. This gives you plenty of time to tick off top attractions including Blue Hole and Cook Island, and also explore neighbourhoods like Eden Pines and Cutthroat Harbour Estates. You could even squeeze in a day trip (or two) from Summerland Key.

How to find the best Summerland Key package deals?

Use Expedia's filter tool to find some terrific Summerland Key package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Summerland Key package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.

Is it cheaper to book a Summerland Key vacation as a package?

You can enjoy significant savings on your Summerland Key retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Summerland Key?

If you're considering an impromptu Summerland Key getaway, browse our last-minute deals that can be booked up to a week before you go. 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 Summerland Key?

  1. Pick your dates: The things you plan to do in Summerland Key and your preferred season can help you decide when to get away.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will likely be the largest expense during your trip to Summerland Key.
  3. Decide how long to go for: Now that you know more about Summerland Key, you can work out the perfect length of your vacation. Create a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Summerland 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.