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

Summerland Key Holidays from £902

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Top Summerland Key flight + hotel deals

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

    Flow Hotel Fort Lauderdale + Flight

    Downtown Fort Lauderdale
    6 nights
    3.5 star property
    9.0/10 - Wonderful (1,005 reviews)
    "Clean room, very spacious, perfect location"
    Reviewed July 28, 2026
    Return London (LON) - Miami (MIA)
    LHR - FLL1 stop FLL - LHR1 stop
    £1,226
    £902
    per traveller
    found 1 day ago
    Flow Hotel Fort Lauderdale
  • 29 Aug - 3 Sept

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

    South Beach
    5 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
    Return London (LON) - Miami (MIA)
    LHR - MIADirect MIA - LHR1 stop
    £13,093
    £6,843
    per traveller
    found 7 hours ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • 10 Oct - 16 Oct

    Pelican Grand Beach Resort - A Noble House Resort + Flight

    East Fort Lauderdale
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,647 reviews)
    "Valet prices are way too high, but everything else was excellent."
    Reviewed July 28, 2026
    Return London (LON) - Miami (MIA)
    LHR - FLL1 stop FLL - LHR1 stop
    £1,332
    £906
    per traveller
    found 1 day ago
    Pelican Grand Beach Resort - A Noble House Resort
  • 10 Oct - 16 Oct

    Hyde Beach House Hollywood Pr Suites + Flight

    Hollywood Beach
    6 nights
    4.0 star property
    6.8/10 - (14 reviews)
    Return London (LON) - Miami (MIA)
    LHR - FLL1 stop FLL - LHR1 stop
    £1,862
    £1,346
    per traveller
    found 1 day ago
    Hyde Beach House Hollywood Pr Suites
  • 10 Oct - 16 Oct

    Riverside Hotel + Flight

    East Fort Lauderdale
    6 nights
    3.5 star property
    9.2/10 - Wonderful (3,160 reviews)
    "I had an amazing stay at the Riverside Hotel in Fort Lauderdale! The location on Las Olas Boulevard is unbeatable, with so many great restaurants, shops, and attractions just steps away. The hotel itself is beautiful, combining historic charm with modern comfort. My room was spotless, comfortable, and well-maintained. The staff was friendly, welcoming, and always willing to help, making the entire experience even more enjoyable. I also loved the relaxing atmosphere around the property and the..."
    Reviewed July 28, 2026
    Return London (LON) - Miami (MIA)
    LHR - FLL1 stop FLL - LHR1 stop
    £1,226
    £905
    per traveller
    found 1 day ago
    Riverside Hotel

Where to stay in Summerland Key

Find the best Summerland Key areas for the activities you enjoy most. Learn more about Summerland Key
Learn more about Summerland Key

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.

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.

Bay Point

While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Florida Keys Beaches.

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 holiday rentals. The neighborhood's tropical charm comes alive with pastel homes on stilts surrounded by palm trees and native plants. A hire 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.

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

What to do in Summerland Key

Summerland Key Hotel Deals

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.

Frequently Asked Questions

Why should I book my Summerland Key holiday with Expedia?

Choose Expedia to arrange your next big adventure simply and all in the same place. Our top tip for getting a great deal on a Summerland Key retreat? Bundle your accommodation, flights and/or hire car into a package holiday. Then add a few exciting tours and activities. Most bookings also come with flexible cancellation policies, so there's no need to panic if you have to switch up your travel plans. Round-the-clock help with making tweaks to your trip is on-hand via our Customer Service Portal link.

When is the best time of year to holiday in Summerland Key?

If you enjoy the atmosphere of peak season, visit Summerland Key in January, February and March. If you'd like a calmer vibe, August, September and October are better times to visit. With daytime average temperatures of 21ºC, January is the coolest period in Summerland Key. The warmest month is August, when you can expect average temperatures of 29ºC throughout the day. Whatever the weather conditions, you'll discover loads to keep you occupied here.

What is the top hotel for my holiday in Summerland Key?

Create lasting memories in Summerland Key by choosing Isla Bella Beach Resort & Spa as your home base and gateway to adventure and exploration.

How do I get a cheap holiday to Summerland Key?

Find flights that suit your schedule, add a hotel to your booking and see how much you save with a Summerland Key holiday. It's as easy as that! From hotels and flights to activities and hire cars, Expedia is where your cheap holiday begins. And with more than 400 partner airlines and 321,000 properties worldwide to choose from, you won't be short of choice. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.

What should I do on my Summerland Key holiday?

Offering must-see tourist attractions such as Florida Keys Beaches and Sugarloaf Beach, a holiday in Summerland Key is packed with fun places to visit. National Key Deer Refuge Visitor Centre and Upper Sugarloaf Key are two other sights also worth checking out.

Do I need a visa for my Summerland Key holiday?

Research the latest rules on official government websites. Your nationality and whether you're visiting for study, leisure or business will determine if you require a visa for Summerland Key. Familiarise yourself with the application process, including the required documentation, fees and turnaround times. Submit your application well in advance to allow sufficient time for processing. Some visas may take several weeks or even months to obtain, depending on the country and time of year.

What should I wear on my Summerland Key holiday?

Although everyone's personal style differs, it can be helpful to have some guidelines for what to bring during your holiday in Summerland Key. Think about looking up social media before leaving for inspiration on fashion trends or dress codes. Daytime temperatures in January, Summerland Key's coolest month, average 21ºC. August marks this city's warmest month when average temperatures reach 29ºC. Our advice? Take the guesswork out of what to pack and check the weather forecast.

What does an Expedia Summerland Key holiday include?

With Expedia, you can select a combination of flights, car hires and hotels to build your ideal Summerland Key travel package. Once you've made your booking, simply add on fun stuff like sightseeing tours and activities. Don't forget, the more you bundle, the more cash you'll save! Private holiday homes and cottages are two of the most sought-after property types in Summerland Key. No matter your holiday style or group size, you can rely on Expedia for the freedom to tailor your next big adventure.

Does Expedia offer Book Now, Pay Later Summerland Key holidays?

Your bank balance shouldn't stop you from going on holiday, so Expedia has come up with a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book a fabulous getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: Klarna offers manageable monthly payment plans that work for all types of budgets, so you can take that well-deserved holiday sooner.
  • No-deposit holidays: Clicking on the "book now" button is much easier with this payment plan. With no upfront fee for your escape, you can Book Now, Pay Later and start packing your suitcase.

Can I choose my airline with a Summerland Key Expedia holiday?

Yes — and it's easy too. Expedia has access to more than 400 partner airlines throughout the world. Our packages give you the flexibility to pick from available flights, hotels and activities that suit you.