Deals on vacations and trips to Upper Matecumbe Key

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Price found within the past 48 hours. Click for updated prices.
May-Dee Suites

May-Dee Suites

2.5 out of 5
Hollywood Hills
Save 100% on your flight
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
An outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A business center, express check-in, and express check-out are also on offer.
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and in-room childcare is an added bonus.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Miami (MIA)
This condo resort features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.
6080 Design Hotel by Eskape Collection

6080 Design Hotel by Eskape Collection

4 out of 5
Mid Beach
Save 100% on your flight
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the a rooftop terrace and perks like a free beach shuttle.
Amazing Apartments at H Beach House

Amazing Apartments at H Beach House

3.5 out of 5
Hollywood Beach
Save 100% on your flight
per person
Jul 17 - Jul 22
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This apartment features 2 outdoor pools and a beach bar. Enjoy the gym and perks like free WiFi. Valet parking is offered and the front desk is staffed around-the-clock.

Top Upper Matecumbe Key hotels deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

4 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $242 per night
$242
per night
Jun 10 - Jun 11
This smoke-free resort features a private beach, a golf course, and a full-service spa. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities.
Hot Tub
Breakfast available
Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $259 per night
$259
per night
Jun 9 - Jun 10
This smoke-free hotel's private beach and 2 outdoor pools are some of the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. There's a computer station and multilingual staff can provide around-the-clock assistance.
Pet friendly
Pool
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $207 per night
$207
per night
Jun 23 - Jun 24
This hotel features a private beach, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the 24-hour gym and perks like free self parking and free WiFi.
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $218 per night
$218
per night
Jul 8 - Jul 9
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. Unwind with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and an area shuttle. You'll appreciate the gym, poolside bar, and laundry facilities.
Breakfast available
Pet friendly
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $221 per night
$221
per night
Jun 24 - Jun 25
The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, and a 24-hour front desk and wedding services are also provided.
Breakfast available
Pet friendly
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $160 per night
$160
per night
Jun 16 - Jun 17
A marina and an outdoor pool are featured at this traditional hotel. Enjoy the free on-the-go breakfast each morning. A business center, a terrace, and a garden are also on offer.
Breakfast included
Pet friendly
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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.

Popular places to visit

Image for Theater of the Sea

Theater of the Sea

4.5/5(215 reviews)

Take the kids to visit the sea life you'll find at Theater of the Sea during your trip to Islamorada. Take in the entertainment choices and beautiful sunsets in this family-friendly area.

Theater of the Sea
Image for Anne's Beach

Anne's Beach

3.5/5(139 reviews)

If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.

Anne's Beach
Image for Founders Park

Founders Park

4.5/5(137 reviews)

Play soccer, baseball and volleyball just meters from the Atlantic Ocean before you dive into the water at this family-friendly beach park.

Founders Park

Photos of local treasures

Islamorada showing a beach bar

Frequently asked questions

How much are vacation packages to Upper Matecumbe Key?
Packages, which include hotels and flights in Upper Matecumbe Key, start from just $295. Make your travel dreams come true and secure your vacation with Travelocity today.
Where can I get the best vacation package deals for Upper Matecumbe Key?
Travelocity is where to go to score a fantastic Upper Matecumbe Key package deal. Choose from 400 partner airlines and 1,000,000 properties all over the globe and create a travel itinerary that’s perfect for you. With so many options, it’s easy to organize your next big adventure.
Why should I book my Upper Matecumbe Key vacation package via Travelocity?
Because life is all about the journey, and we have everything you need to get you on your way. With our superb service and Price Match Guarantee, you can book your trip with confidence. Plus, you can sleep easy on the road knowing you can reach us with our 24/7 support.
Will I save money on my Upper Matecumbe Key car rental if I book it with my hotel or flight?
Definitely. And our Upper Matecumbe Key vacation packages will help you do it. With just a few clicks you can save cash and time by bundling your bookings. Pick up the keys to your rental car then set your own course. Searching for things to do? Throw some tours or experiences into your package and make savings on those too.
What is the best time of year to go to Upper Matecumbe Key?
You’ll pick up the lowest hotel prices in and pay the highest prices during . You can expect it to be more relaxed in February, September and October, while you’ll find a lot more fellow tourists to hang out with during the months of January, March and November. It comes down to what prices you’re willing to pay, the weather conditions and how well you deal with crowds.