Upper Matecumbe Key Beach Vacations

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Flight and Beach hotel deals in Upper Matecumbe Key

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Bay Breeze Premium Apartments By Eskape Collection
MirabileCondoDwntown MIA Brickell w PRKG
The Retreat Collection at 1 Hotel & Homes South Beach
Miami Downtown Condos
1 Hotel South Beach
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5* Beach holidays in Upper Matecumbe Key

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MirabileCondoDwntown MIA Brickell w PRKG
The Retreat Collection at 1 Hotel & Homes South Beach
Miami Downtown Condos
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3 Night Beach holidays in Upper Matecumbe Key

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Marenas Beach Resort
MirabileCondoDwntown MIA Brickell w PRKG
The Retreat Collection at 1 Hotel & Homes South Beach
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4 Night Beach holidays in Upper Matecumbe Key

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Family Pool Home by Hollywood Beach
3BR Pool House Sleeps 8
MirabileCondoDwntown MIA Brickell w PRKG
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Find the best beach vacations in Upper Matecumbe Key

What are some benefits when booking beach vacations in Upper Matecumbe Key?

When you travel to the beach in Upper Matecumbe Key, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.


How can I book the best beach vacations in Upper Matecumbe Key?

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Upper Matecumbe Key trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Upper Matecumbe Key?

There are quite a few things you can do to get cheap beach vacations in Upper Matecumbe Key. Prices range from CA $932, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Upper Matecumbe Key. These package deals let you save by booking your accommodation and your flight together with savings of up to 39.

Why should I book family beach vacations?

When you're travelling with the family to Upper Matecumbe Key, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Upper Matecumbe Key?

It's easy to find a beachfront vacation accommodation in Upper Matecumbe Key using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Upper Matecumbe Key as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Upper Matecumbe Key is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Islamorada. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

Beach Hotels in Upper Matecumbe Key

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
  • 5 min drive from Bud n' Mary's Dive Center
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,330 reviews)
Exelente service but the room need more clean and attention

Reviewed on May 11, 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
  • 10 min drive from Bud n' Mary's Dive Center
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,740 reviews)
The Villas are great! Nice and clean/ modern We had an amazing time with my elderly parents and my litte kids.

Reviewed on May 12, 2026

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
  • 6 min drive from Bud n' Mary's Dive Center
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,014 reviews)
Everything about this property was excellent, from the wonderful staff to the kid-friendly atmosphere. We loved the breakfast brunch and the overall vibe of the place. However, dinner at The Drift was a letdown. For the price, the quality just wasn't there. I’d highly recommend the stay, but I suggest ...

Reviewed on May 10, 2026

Islander Resort
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.

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