Title: Summerland Key Cheap Vacations 2026 | Expedia.com

![](https://images.trvl-media.com/place/6177802/bda449a1-0506-4d80-94a6-fb19766bc7f4.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Summerland Key Cheap Vacations

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## Top Cheap vacation packages in Summerland Key

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

![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$872

per person

May 24 - May 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,825 reviews)

Beautiful place Our patio door wouldn’t close , stayed on the first floor so it was a little uncomfortable. Room service forgot to leave fresh towels, never refills Kcup coffee, when asked receptionist they gave us tea. Nice and comfortable room without even a spoon, so why have a kitchen? They had a rib cook off on Sunday then a wedding on Thursday so not for people trying to enjoy the resort and rest.

Reviewed on Mar 16, 2026

![Villas At Hawks Cay Resort](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8638cc9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Villas At Hawks Cay Resort

Save 100% on your flight

$1,267

per person

May 19 - May 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (174 reviews)

Property was clean and staff were helpful. Would stay again.

Reviewed on Mar 11, 2026

![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$878

per person

May 19 - May 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (1,004 reviews)

We Love this place!

Reviewed on Mar 17, 2026

Don't see what you're looking for?

See all available trips from Columbus to Summerland Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Cheap vacations in Summerland Key

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

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,320

per person

May 19 - May 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,308 reviews)

We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window

Reviewed on Mar 12, 2026

Don't see what you're looking for?

See all available trips from Columbus to Summerland Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Cheap vacations in Summerland Key

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

![Kimpton Surfcomber Hotel by IHG](https://images.trvl-media.com/lodging/1000000/20000/16000/15996/93c84cb9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kimpton Surfcomber Hotel by IHG

South Beach

Save 100% on your flight

$1,004

per person

May 29 - Jun 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,007 reviews)

Smallish rooms but very clean and fabulous outdoor amenities including pool and restaurant bar.

Reviewed on Mar 10, 2026

![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1 Hotel South Beach

South Beach

Save 100% on your flight

$1,692

per person

May 29 - Jun 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,455 reviews)

This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again!

Reviewed on Mar 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to Summerland Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Cheap vacations in Summerland Key

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

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Creekside Inn

Save 100% on your flight

$733

per person

May 19 - May 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.8/10 Good! (1,027 reviews)

Older, but near our kayaking. On the canal & near several restaurants- walkable. Quiet, cool

Reviewed on Mar 16, 2026

![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/f54c02bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Casablanca Miami Beach

North Beach

$2,565

per person

May 21 - May 25

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.8/10 (321 reviews)

Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

Don't see what you're looking for?

See all available trips from Columbus to Summerland Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Find amazing cheap vacations in Summerland Key

####  How can I find budget-friendly Summerland Key vacation packages on Expedia? 

 Playing around with the easy-to-use search wizard is one of the best ways to find affordable Summerland Key vacation packages on Expedia. Tap your dates in and it'll offer some of the cheapest Summerland Key getaways within seconds. You can also use the maximum price filter to view deals within your budget. If you're traveling during peak season dates, it's a good idea to book early to snag some of the best offers. You may score irresistible [last-minute specials](https://www.expedia.com/lp/b/vacations/last-minute-deals) for travel in low season. 
  
####  How to find cheap last-minute Summerland Key travel deals? 

 On Expedia's [last-minute](https://www.expedia.com/lp/b/vacations/last-minute-deals) travel deals page, you'll encounter a plethora of special offers for late vacations to Summerland Key. Remember, you're more likely to bag savings on last-minute travel during off-peak periods. Consider checking different departure dates, too. Expedia's nifty search tool lets you compare some of the best last-minute Summerland Key vacation packages. The handy filters let you tailor your trip according to your preferences, including hotel star rating, amenities, and property location. 
  
####  When is the best time to visit Summerland Key on a budget? 

 For some of the cheapest vacation packages to Summerland Key from $733, it's best to travel during low season dates. With fewer people traveling during these periods, flights and hotels usually have lower prices. It's also a good idea to avoid popular travel times. These include spring break, Thanksgiving, and other federal holidays. On Expedia, you'll encounter some of the best travel deals to Summerland Key. Best of all, vacation [payment plans](https://www.expedia.com/lp/b/vacations/planning) mean you can spread the cost of your trip over 3, 6, or 12 months. 
  
####  Can I cancel my Summerland Key vacation package booking? 

 Yes, many of Expedia's cheap Summerland Key getaway packages allow for free cancellation in case your plans change. Follow the easy steps to cancel by logging into your Expedia account and clicking on “Trips” page'. Keep in mind, though, that each vacation package has different cancellation policies, so be sure to look over them before booking. The good news is you'll clearly see this information on Expedia when you book. There's even a free cancellation search filter that lets you view flexible vacations to Summerland Key. 
  
####  Why should I book my Summerland Key vacation with Expedia? 

 A multitude of exclusive travel deals you won't find anywhere else is one of the top reasons to book your cheap Summerland Key vacation package with Expedia. And with one of the widest choices of flights and hotels available, you'll easily find the right trip for you. The handy search wizard and filters let you compare hundreds of great deals in seconds, too. It's not only the cheap prices either: Expedia's booking protection and 24/7 support give you peace of mind before and during your 2026 trip. 
  
####  How to find cheap Summerland Key vacation packages on Expedia? 

 When searching for budget vacations to Summerland Key, look out for the green savings label. This indicates you've snagged a deal only available on Expedia. Another popular way of getting money off your 2026Summerland Key vacation is by joining [One Key](https://www.expedia.com/welcome-one-key). Expedia's amazing reward program gives you access to hundreds of member-only discounts on select hotels. Keep a look out for the blue savings label in the search results. Best of all, One Key is free to join. 
  
####  Why should I book a package to Summerland Key? 

 You'll often snag package savings on your Summerland Key vacation when bundling together your flights and accommodation. Expedia even shows you how much you're saving by booking a package. It's not just cheaper prices, either. Packages often have more flexible booking conditions, meaning you're more likely to get a refund in case your 2026 plans change. While booking flights and hotels separately usually requires full payment, Summerland Key vacation packages often let you pay a small upfront deposit to confirm. 
  
####  How to plan a cheap vacation to Summerland Key? 

Settling on your dates is usually the first step to planning an affordable Summerland Key getaway. If you're traveling during peak season dates, it's a good idea to book your trip in advance. This way, you're more likely to bag early-bird deals. Don't rule out a [last-minute travel deal](https://www.expedia.com/lp/b/vacations/last-minute-deals) for low season dates, though. Once you've picked your dates, tap them into the search wizard to see some of the best Summerland Key vacation package deals. Hop over to Expedia's [vacation planning page](https://www.expedia.com/lp/b/vacations/planning) for more tips for your dream vacation. 

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## More Vacation Ideas

[Flights to Summerland Key

](https://expedia.com/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[

Summerland Key Hotels

](https://expedia.com/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[

Vacation Rentals in Summerland Key

](https://expedia.com/Summerland-Key-Vacation-Rentals.d6177802.Travel-Guide-VacationRentals)[

Car Rentals in Summerland Key

](https://expedia.com/Car-Rentals-In-Summerland-Key.d6177802.Car-Rental-Guide)[

Summerland Key Vacations

](https://expedia.com/Summerland-Key.d6177802.Destination-Travel-Guides)[

Things to do in Summerland Key

](https://expedia.com/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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