Compare Upper Matecumbe Key Resorts

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Resorts in Upper Matecumbe Key

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$304 nightly
The price is $342 total per night
$342 total
Jul 5 - Jul 6
Total with taxes and fees
Cheeca Lodge & Spa features a private beach, a golf course, and a full-service spa. Free valet and self parking are available, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, luggage storage, and securing valuables. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
On private beach
Pool
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
$295 nightly
The price is $332 total per night
$332 total
Jun 22 - Jun 23
Total with taxes and fees
Guests of Baker's Cay Resort Key Largo, Curio Collection by Hilton have access to a private beach, 2 outdoor pools, and a gym. Parking is available for USD 23 per night (USD 35 per night for valet parking), and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with luggage storage, securing valuables, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a hot tub, a conference center, and a 24-hour business center.
On private beach
Pool
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$247 nightly
The price is $278 total per night
$278 total
Jul 6 - Jul 7
Total with taxes and fees
At Amara Cay Resort, guests enjoy a private beach, an outdoor pool, and a gym. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a meeting room, a terrace, and laundry facilities.
On private beach
Pool
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
68500 Overseas Hwy Long Key FL
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $224 total per night
$224 total
Jun 14 - Jun 15
Total with taxes and fees
At Lime Tree Bay Resort, guests have access to a private beach, 3 outdoor pools, and free WiFi in public areas. If you drive, take advantage of free parking. The front desk has multilingual staff that can help with tours/tickets and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include an outdoor tennis court, coffee/tea in a common area, and free use of bicycles.
On private beach
Pool
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4.5 out of 5
97450 Overseas Highway Key Largo FL
Free Cancellation
Reserve now, pay when you stay
$312 nightly
The price is $351 total per night
$351 total
Jun 28 - Jun 29
Total with taxes and fees
Guests of Playa Largo Resort & Spa, Autograph Collection have access to a marina, a full-service spa, and an outdoor pool. Valet parking is offered for USD 39.38 per night. Multilingual staff at the 24-hour front desk can assist with tours or tickets, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a 24-hour gym, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$336 nightly
The price is $378 total per night
$378 total
Jul 7 - Jul 8
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort features a private beach, a marina, and 3 outdoor pools. Transportation is made easy with a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with luggage storage and tours/tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a 24-hour gym, free WiFi in public areas, and meeting rooms.
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
$238 nightly
The price is $268 total per night
$268 total
Jul 8 - Jul 9
Total with taxes and fees
Guests of La Siesta Resort & Villas have access to a private beach, a marina, and an outdoor pool. Transportation is made easy with a free area shuttle. The 24-hour front desk has staff always at the ready. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a terrace, a picnic area, and wedding services.
On private beach
Pool
Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
61 Hawks Cay Boulevard Marathon FL
Free Cancellation
Reserve now, pay when you stay
$747 nightly
The price is $840 total per night
$840 total
Jun 15 - Jun 16
Total with taxes and fees
Villas At Hawks Cay Resort features a private beach, a marina, and a full-service spa. You can take advantage of limited parking, along with limo/town car service. The 24-hour front desk has multilingual staff ready to assist with concierge services and securing valuables. Other amenities at this beach resort include 3 outdoor pools, a gym, and a sauna.
On private beach
Pool
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
Guests staying at Matecumbe Resort enjoy access to a private beach, an outdoor pool, and free WiFi in public areas. You can put free parking to good use if you drive. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing. Other amenities at this beach resort include free use of bicycles, laundry facilities, and a garden.
On private beach
Pool
Don't see what you're looking for?
See all available properties in Upper Matecumbe Key
View all properties
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.

Hotel Options in Upper Matecumbe Key

    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82 Islamorada FL
    $304 nightly
    The price is $342 total per night from Jul 5 to Jul 6
    $342 total
    Jul 5 - Jul 6
    Total with taxes and fees
    9.2/10 Wonderful! (1,325 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy Islamorada FL
    $230 nightly
    The price is $258 total per night from Jun 18 to Jun 19
    $258 total
    Jun 18 - Jun 19
    Total with taxes and fees
    9.2/10 Wonderful! (1,753 reviews)
    Islander Resort

    Islander Resort

    82100 Overseas Highway Islamorada FL
    $316 nightly
    The price is $356 total per night from Jun 21 to Jun 22
    $356 total
    Jun 21 - Jun 22
    Total with taxes and fees
    9.4/10 Exceptional! (1,050 reviews)

Resort Hotels

Resort hotels in Upper Matecumbe Key
Find your next great getaway when you book at a resort hotel in Upper Matecumbe Key. Resorts are great for families or couples, or even solo travelers looking for a piece of paradise. Sure, you can leave your hotel and explore Upper Matecumbe Key at your leisure…but with everything these sorts of hotels offer, you may never want to. From food and shopping to entertainment and organized tours, a resort hotel in Upper Matecumbe Key is a great way to score an amazing vacation—and Orbitz can help you get there.

Resort hotels for everyone in Upper Matecumbe Key
If you’re traveling with the kids, you know how hard it is to keep them entertained. Let them have some fun on their own: some resorts have clubs for the kiddos, including kid-friendly pools and adventure camps where they can explore, do some crafts and even take part in learning activities. (Don’t worry, no one will tell them this vacation is actually educational.) Of course, there’s plenty for adults to do at Upper Matecumbe Key resorts as well. Take a yoga class, book a few treatments at the spa, or do a little shopping. Go ahead, charge it to the room. You’re on vacation!

Ready to wow your special someone? Plan a romantic getaway complete with luxury accommodations. Surprise your partner with a couples massage, followed by a candlelit dinner at the 5-star on-site hotel. Some of these luxury hotels even have adults-only pools with swim-up bars so you can float about with a couple of cocktails, watching the sunset and enjoying your time together.

Upper Matecumbe Key Resorts essential information

Accommodation
12 Resorts
Lowest Price
$224
Highest Price
$840
Popular accommodation
Cheeca Lodge & Spa, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Amara Cay Resort, Lime Tree Bay Resort, Playa Largo Resort & Spa, Autograph Collection, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, La Siesta Resort & Villas, Villas At Hawks Cay Resort, Matecumbe Resort

More to Explore