Summerland Key Holidays from £811

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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!

Top Summerland Key Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
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
16 Sept - 21 Sept
found 3 hours ago
Return direct flight included
London (LON) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
The hotel overall aesthetics was very nice. The parking charge was steep. The pool area is limited & fills up quickly. The staff was absolutely fantastic & really what makes this place stand out from others. Everyone I encountered was so friendly & helpful. Especially the hard working beach staff. I didn't use their internet while there so can't comment on it. Bed was standard comfortable. Minor things that bothered me was a roach in my bathroom the first night but it's Florida in the summer. It was just one. It happens, I guess. The cloth couch cushion had a questionable stain. I flipped it over & avoided it. The towels had a weird smell.

Reviewed on 29 Jul 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
3 Oct - 10 Oct
found 13 hours ago
Return direct flight included
London (LGW) to Miami (MIA)
8/10 Very Good! (1 review)
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Save 100% on your flight
per person
4 Sept - 9 Sept
found 24 hours ago
Return direct flight included
London (LON) to Miami (MIA)
9.6/10 Exceptional! (5 reviews)
Quiet.Lobby was nice and smelled amazing. Staff was good. Loved the gym/studio. Dislikes: No hot water in the shower. Lobby smelled amazing but wasn’t consistent throughout the building.

Reviewed on 17 Jul 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
13 Oct - 20 Oct
found 17 hours ago
Return direct flight included
London (LGW) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
loved everything about it

Reviewed on 28 Jul 2025

Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
11 Oct - 18 Oct
found 1 hour ago
Return direct flight included
London (LON) to Miami (MIA)
9/10 Wonderful! (2,401 reviews)
A great stay! Beds are a little firm, bathrooms a little small and the parking garage elevator being serviced were all outdone by the excellent service and quaintness for this hotel.

Reviewed on 28 Jul 2025

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
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

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

Top hotels in Summerland Key

Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is £126 per night from 26 Aug to 27 Aug
£126
26 Aug - 27 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Sarah was AWESOME"

Reviewed on 29 Jul 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
9.6/10 Exceptional! (418 reviews)
Perfect
"Reviews here are spot on. Loved the quality of this Villa. Staff is so friendly. Will stay here again anytime we visit the Keys."

Reviewed on 23 Jul 2025

Get rates
Sugarloaf Key Hotel at KOA Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is £83 per night from 17 Aug to 18 Aug
£83
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"It was great"

Reviewed on 27 Jul 2025

Sugar Loaf Lodge
See all 596 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

What 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
Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

£491
per traveller
Marathon Backcountry Fishing Charter
12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

£20
per adult
78% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
See all activities in Summerland Key

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.

* 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.