COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Check restrictions for your trip.Opens in new tab or window

Holidays to Summerland Key

Choose two or more items and save on your trip:

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

Garden Inn Homestead

Garden Inn Homestead

2.5 out of 5

£590

per person
14 Jun - 18 Jun
Return flight included
London (LON) to Miami (MIA)
3.4/5 (1,070 reviews)

"It was a fine hotel for the price. Mostly clean, little grab bag for breakfast.…"

Reviewed on 1 Apr 2021

Fairway Inn Florida City / Homestead / Everglades

Fairway Inn Florida City / Homestead / Everglades

2.5 out of 5

£598

per person
14 Jun - 18 Jun
Return flight included
London (LON) to Miami (MIA)
4.3/5Excellent! (1,666 reviews)

"Clean, safe, nice staff. The property is old, but nice.…"

Reviewed on 10 Apr 2021

The L Hotel

The L Hotel

3 out of 5
Mid Beach

£650

per person
14 Jun - 18 Jun
Return flight included
London (LON) to Miami (MIA)
4/5Very Good! (836 reviews)

"Small and quiet, but missing some of the basics. No full length mirror, no ironing board, no housekeeping service. We stayed for 4 nights and no cleaning.…"

Reviewed on 9 Apr 2021

UP MIDTOWN HOTEL

UP MIDTOWN HOTEL

2 out of 5
Midtown

£603

per person
14 Jun - 18 Jun
Return flight included
London (LON) to Miami (MIA)
1.9/5 (337 reviews)

"perfect for an overnight stay.…"

Reviewed on 1 Apr 2021

EAST Miami

EAST Miami

4.5 out of 5
Brickell

£763

per person
14 Jun - 18 Jun
Return flight included
London (LON) to Miami (MIA)
4.4/5Excellent! (1,111 reviews)

"Great location! Beautiful hotel, so clean. They have valet parking but it is kind of expensive. Otherwise everything was perfect!…"

Reviewed on 9 Apr 2021

Comfort Inn & Suites Downtown Brickell-Port of Miami

Comfort Inn & Suites Downtown Brickell-Port of Miami

2.5 out of 5
Downtown Miami

£665

per person
14 Jun - 18 Jun
Return flight included
London (LON) to Miami (MIA)
3.2/5 (641 reviews)

"Good for the price paid…"

Reviewed on 8 Apr 2021

Top Hotel Deals

Kelly's Kabin Private Cottage on Summerland Key
Kelly's Kabin Private Cottage on Summerland Key
24253 Overseas Hwy, Summerland Key, FL
The price is £644 per night from 3 May to 4 May

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! (22 reviews)
Spot on

"Quiet location, super clean with convenient arrival and departure, hosts were quick to respond. We will be back!"…"

Reviewed on 26 Mar 2021

Kelly's Kabin Private Cottage on Summerland Key
New Listing! Summerland Canal-front Escape W/ Pool 2 Bedroom Home
New Listing! Summerland Canal-front Escape W/ Pool 2 Bedroom Home
3.5 out of 5
138 Airport Dr S, Summerland Key, FL

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

New Listing! Summerland Canal-front Escape W/ Pool 2 Bedroom Home
Florida Keys Waterfront House W/pool & Spectacular Ocean Views/minimum 28 Nights
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

Florida Keys Waterfront House W/pool & Spectacular Ocean Views/minimum 28 Nights
See all 516 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

Image for Kayak / Paddleboard Backcountry Tours

Kayak / Paddleboard Backcountry Tours

£51
Per adult
100% of travellers recommend
Kayak / Paddleboard Backcountry Tours
Image for Private Fishing Charters 34 Ft Contender ST-Center Console

Private Fishing Charters 34 Ft Contender ST-Center Console

£586
Per adult
Private Fishing Charters 34 Ft Contender ST-Center Console
Image for Kayak/Paddleboard Backcountry Tour

Kayak/Paddleboard Backcountry Tour

£51
Per adult
Kayak/Paddleboard Backcountry Tour
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

If I'm not able to travel, can I cancel my Summerland Key holiday package?
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.
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.