Summerland Key Holidays from £816

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Your Summerland Key Holiday

The hassle-free way to experience this interesting city is with a tailor-made Summerland Key holiday package. Base yourself in the neighbourhood 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 travelling. Browse the wide range of options on Expedia today and put your Summerland Key holiday plans in motion!

The Latest Summerland Key Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
per person
23 Aug - 30 Aug
found 12 hours ago
Return flight included
London (LON) to Miami (MIA)
9/10 Wonderful! (128 reviews)
Great place and good value. Only complain, they should put black out at the bedroom! To bright in the morning.

Reviewed on 19 Jun 2025

The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
per person
4 Sept - 11 Sept
found 10 hours ago
Return direct flight included
Edinburgh (EDI) to Miami (MIA)
9.6/10 Exceptional! (4 reviews)
Everything was amazing- The accommodations, the property decor, the staff like Adrian and Chef Luis were very personable and welcoming. Our room was upgraded from partial ocean view to full as we were celebrating our 23rd wedding anniversary, so that was a nice touch. We would definitely book again.

Reviewed on 31 May 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
4 Sept - 10 Sept
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Miami (MIA)
8/10 Very Good! (1 review)
iCoconutGrove Vacation Rentals

iCoconutGrove Vacation Rentals

4 out of 5
Coconut Grove
Save 100% on your flight
per person
18 Sept - 25 Sept
found 1 day ago
Return flight included
London (LGW) to Miami (MIA)
9.2/10 Wonderful! (1,003 reviews)
Very relaxing, & private. Loved it! Very easy to get ahold of management for any needs.

Reviewed on 22 Jun 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
13 Sept - 20 Sept
found 1 hour ago
Return direct flight included
Edinburgh (EDI) to Miami (MIA)
8.6/10 Excellent! (1,107 reviews)
This was our second time staying in this property and we would stay here every time! It’s clean it’s comfortable. The service is great. You cannot beat the view. We love it here! Only thing is try not to get a room by the elevators. It’s super loud.

Reviewed on 1 Jul 2025

EAST Miami Residences

EAST Miami Residences

5 out of 5
Downtown Miami
Save 100% on your flight
per person
4 Sept - 10 Sept
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Miami (MIA)
9/10 Wonderful! (63 reviews)
No me gustó el sector ya que hay mucho ruido en la calle motos carros acelerando No deja dormir La habitación me gustó bastante pero no logré Disfrutarla

Reviewed on 23 May 2025

Summerland Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Max Temp Winter
24ºC
Max Temp Summer
29ºC
Top Sights
Bahia Honda State Park, Florida Keys Beaches and Calusa Beach

Our guide on where to stay in Summerland Key

Check out a few of the areas and neighbourhoods we love in Summerland Key Learn more about Summerland Key
Default Image

Cutthroat Harbor Estates

While there might not be top attractions in Cutthroat Harbor Estates, you can explore the larger area and discover places like Venture Out Keys and Upper Sugarloaf Key.

Find hotels in Cutthroat Harbor Estates

Our pick of the best Summerland Key Hotel Deals

Parmer's Resort
Parmer's Resort
2.5 out of 5
565 Barry Avenue, Summerland Key, FL
Stay at this beach motel in Summerland Key. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
8.8/10 Excellent! (1,002 reviews)
Great stay with excellent staff, service, rooms!
"A wonderful stay! Great staff, service, and rooms! Very comfy bed with lamps on both sides for reading. Great shower and kitchen! Breakfast was much more than “Grab and Go. We held a large family event here and Parmer’s couldn’t be more accommodating."

Reviewed on 22 Jun 2025

Parmer's Resort
Sugarloaf Key Hotel at KOA Resort
Sugarloaf Key Hotel at KOA Resort
3 out of 5
251 Co Rd 939, Summerland Key, FL
Stay at this 3-star hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a private beach. Our guests praise the helpful staff and the clean rooms in their ...
9.6/10 Exceptional! (396 reviews)
"Our hotel suite was perfect. Very clean, stylish, and functional. The pool was amazing and we especially loved the hammocks under the palm trees. There were iguanas hanging by the pool when it wasn’t busy and the bar is open most all day. The beach was okay. Good for sunning I guess but the water ..."

Reviewed on 29 Jun 2025

Sugarloaf Key Hotel at KOA Resort
Looe Key Reef Resort
Looe Key Reef Resort
2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the bar and the helpful staff in their reviews. ...
7.4/10 Good! (1,001 reviews)
"Very cute hotel. The rooms are recently renovated."

Reviewed on 12 Jun 2025

Looe Key Reef Resort
See all 604 properties in Summerland 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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.

Unmissable things to do in Summerland Key

A fun-filled adventure for the whole family

Guided Clear Kayak Eco-Tour Near Key West

£58
per adult
Guided Clear Kayak Eco-Tour Near Key West
Full Day Charter Snorkeling Sandbar and Eco Safari Adventure

Full Day Charter Snorkeling Sandbar and Eco Safari Adventure

£665
per traveller
Full Day Charter Snorkeling Sandbar and Eco Safari Adventure
Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

£493
per traveller
Marathon Backcountry Fishing Charter
See all activities in Summerland Key

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.