Summerland Key Holidays from £854

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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.
President Hotel

President Hotel

3.5 out of 5
South Beach
Price was £1,343, price is now £854 per person
£854
per person
15 Jan - 21 Jan
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
8.4/10 Very good! (2,874 reviews)
Everyone was nice helpful and accommodating! The room was clean and location was good.

Reviewed on 29 Oct 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was £1,482, price is now £910 per person
£910
per person
15 Jan - 21 Jan
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
8.4/10 Very good! (2,021 reviews)
Great overall!

Reviewed on 28 Oct 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was £1,460, price is now £917 per person
£917
per person
15 Jan - 21 Jan
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was £4,474, price is now £2,847 per person
£2,847
per person
17 Dec - 24 Dec
found 15 hours ago
Return flight included
London (LON) to Miami (MIA)
9.4/10 Exceptional! (1,682 reviews)
This was a follow-on visit after a wonderful stay last month. The hotel policies are not at concierge 5-star level. They’re vanilla 4-star which don’t match the price.

Reviewed on 28 Oct 2026

Miami Vacation Rentals - Downtown

Miami Vacation Rentals - Downtown

5 out of 5
Downtown Miami
Save 100% on your flight
Price was £1,658, price is now £1,071 per person
£1,071
per person
9 Dec - 14 Dec
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
9/10 Wonderful! (111 reviews)
Great place. I would definitely come again!

Reviewed on 29 Oct 2026

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
A calm lake with several white birds, including herons and pelicans, on the water's edge.

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 Key and Venture Out Keys.

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 £135 per night from 1 Nov to 2 Nov
£135
1 Nov - 2 Nov
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"The privacy was fantastic, the staff was helpful and we were right down the street from Robbie’s"

Reviewed on 28 Oct 2026

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
Get rates
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
Fully refundableReserve now, pay when you stay
The price is £122 per night from 17 Nov to 18 Nov
£122
17 Nov - 18 Nov
includes taxes & fees
Looe Key Reef Resort
See all 651 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

Stay near popular Summerland Key attractions

Sugarloaf Beach

8.4/10 (38 reviews)
This secluded private beach on Sugarloaf Key offers a tranquil escape from the busier Florida Keys shorelines. Guests enjoy pristine views and peaceful sunbathing in a natural, amenity-light setting.
See properties

What to do in Summerland Key

12 hours Day at Key West With Boat Tour and Snorkeling

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

£25
per adult
82% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Kayak the mangrove tidal creeks

Key West Mangrove Kayak Eco Tour

£60
per adult
100% of travellers recommend
Key West Mangrove Kayak Eco Tour
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

£30
per adult
88% of travellers recommend
Key West Conch Tour Train
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.

Explore a world of travel with Expedia

* 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.