When is the best time of year to visit Summerland Key?

You'll need to consider your priorities to find the right answer. Typically, you'll land the best deals in , while is when hotel rates usually rise. Summerland Key is at its busiest in . If you want a more laid-back getaway, would be a better time to pack your bags.

How far in advance should I book my Summerland Key holiday?

It depends on the airline, but you can normally compare international fares on Expedia up to 12 months in advance. While it's generally recommended to book ahead of time, lucky customers will occasionally nab a cheaper flight just weeks before departure dates.

What should I know before booking a Summerland Key travel package?

Our prices are always low. However, you'll pick up an even better deal when you book your hotels, flights and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a great range of choice.

Does Expedia offer Book Now, Pay Later Summerland Key holiday packages?

If the reason for your travel has cropped up unexpectedly, Expedia can help take the financial load off your shoulders. Working in conjunction with online lender Affirm, we offer a Book Now, Pay Later option for all holiday package bookings. It's easy to set up a payment arrangement for your travel that works for you.

Holidays to Summerland Key

Accommodation, flights, car rentals, things to do and more - for your holiday in Summerland Key choose Expedia! Find everything you need to organise your trip to Summerland Key in one place. Enter your dates in the search bar above or scroll to our top deals below!

Top flight + hotel deals in Summerland Key

The Alexander Hotel

Mid Beach

£765

per person

23 Jun - 27 Jun

Return flight included

London (LON) to Miami (MIA)

3/5 (771 reviews)

nice location need more elevators had to wait forever. rooms were ok could be cleaner

Reviewed on 21 Mar 2021

Garden Inn Homestead

£471

per person

31 May - 2 Jun

Return flight included

London (LON) to Miami (MIA)

3.4/5 (1,070 reviews)

they left me alone when I asked and were very quiet

Reviewed on 13 Apr 2021

Fairway Inn Florida City / Homestead / Everglades

£474

per person

31 May - 2 Jun

Return flight included

London (LON) to Miami (MIA)

4.3/5Excellent! (1,666 reviews)

The property is not glamorous but it is clean which really matters to me. The phone in my room did not work. The leather chair also looked like it had been chewed on. However, it’s a cheaper property and you get what you pay for so I knew what to expect. If you want a cheaper place to stay that’s clean, this is a decent choice.

Reviewed on 21 Apr 2021

Super 8 By Wyndham Florida City/Homestead/Everglades

£475

per person

31 May - 2 Jun

Return flight included

London (LON) to Miami (MIA)

3.9/5Good! (998 reviews)

great service perfect for vacation time thinking time in a great place for a relaxing peace of mind.

Reviewed on 5 Apr 2021

Days Inn by Wyndham Florida City

£478

per person

31 May - 2 Jun

Return flight included

London (LON) to Miami (MIA)

2.9/5 (1,005 reviews)

The whole area felt safe even though we stayed for 1 night. The hotel was very clean, staff was great, overall had a great experience.

Reviewed on 6 Apr 2021

Travelodge by Wyndham Florida City/Homestead/Everglades

£483

per person

31 May - 2 Jun

Return flight included

London (LON) to Miami (MIA)

4.4/5Excellent! (1,490 reviews)

Clean,comfortable room, floor was updated by vinyl plank ,whicj gives room nice modern clean look! It's good basic hotel with parking enclude. Due to Covid19 they don't serve breakfast -paper bag luch which is: bottle of water ,orange( mine was spoiled) muffin in tetrabag and granola bar. I wish they would update website and mentioned it,bevause i booked it with early available breakfast. Other than that its good place to stay,pleanty places to eat and quite.

Reviewed on 19 Apr 2021

Top Hotel Deals

Kelly's Kabin Private Cottage on Summerland Key

24253 Overseas Hwy, Summerland Key, FL

Situated in Summerland Key, this cottage is within 9 miles (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound and National Key Deer Refuge Visitor Center. ...

4.9/5Exceptional! (24 reviews)

Perfect cottage

"We had an exceptional stay at Kelly’s Kottage (6 night/7 days). It was just as described. It has a fully functioning kitchen with all the items you need to make a meal. A sitting area with a dining room table for four as well as a room to watch tv or just sit and read a good book. The bedroom has ..."

Reviewed on 21 Apr 2021

Florida Keys Waterfront House W/pool & Spectacular Ocean Views/minimum 28 Nights

25375 4th St, Summerland Key, FL

Situated in Summerland Key, this holiday home is within 9 miles (15 km) of National Key Deer Refuge Visitor Center, Upper Sugarloaf Key and Upper Sugarloaf Sound. ...

3/5 (2 reviews)

Very Disappointed!! Renters BEWARE!!

"Our family has visited the Fl Keys annually for 15 years and we have never had any issues with rental homes. We rented this house as a last-minute reservation since it hadn't been rented for the month of June and was given a reduced rate since we weren't renting it for a full 28 days. We have the ..."

Reviewed on 27 Jul 2020

Forever Summer

1051 Caribbean Dr E, Summerland Key, FL

Situated on the waterfront, this holiday home is within 9 miles (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound and National Key Deer Refuge Visitor Center. ...

See all 509 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.

Top things to do in Summerland Key

Kayak / Paddleboard Backcountry Tours

£50

Per adult

100% of travellers recommend

Private Key West Fishing Charter on 34 Ft Contender

£579

Per adult

Kayak/Paddleboard Backcountry Tour

£51

Per adult

See all activities in Summerland Key

Plan your Summerland Key holiday with Expedia

Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
We have selected for you amazing deals on incredible hotels in Summerland Key. Have a look simply by using the search bar above.
Most hotels come with free cancellation* , because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page.
Start browsing now!

*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

We totally get that life can throw you the odd curveball. If you’ve locked in a Summerland Key holiday package and need to cancel or amend it, we’re here to help. It’s always worth looking up our Customer Service Portal first for information. But in general, if you’ve taken out your package in the last 24 hours, you may be able to cancel and rebook at no cost. If it’s been longer than 24 hours, your hotel, airline or car rental company may impose a fee.

Holidays to Summerland Key

Travellers

Room 1

Top flight + hotel deals in Summerland Key

The Alexander Hotel

£765

Garden Inn Homestead

£471

Fairway Inn Florida City / Homestead / Everglades

£474

Super 8 By Wyndham Florida City/Homestead/Everglades

£475

Days Inn by Wyndham Florida City

£478

Travelodge by Wyndham Florida City/Homestead/Everglades

£483

Top Hotel Deals

Top things to do in Summerland Key

Kayak / Paddleboard Backcountry Tours

Private Key West Fishing Charter on 34 Ft Contender

Kayak/Paddleboard Backcountry Tour

Plan your Summerland Key holiday with Expedia

Frequently asked questions

Hotels

Flights

Cars

Packages

Holiday Rentals