Hotels in Upper Matecumbe Key

Name: Waterside Suites & Marina
Price range: $166 total

Search over 2,826 hotels from $166

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Apr 6 - Apr 7

Tonight

Apr 7 - Apr 8

Tomorrow night

Top Rated Upper Matecumbe Key Hotels

Free Cancellation

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0.09 mi from city center

$315 nightly

$354 total

Apr 22 - Apr 23

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 securing valuables, luggage storage, and dry cleaning/laundry. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.

On private beach

Pool

Free Cancellation

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1.76 mi from city center

$269 nightly

$303 total

May 7 - May 8

Total with taxes and fees

Chesapeake Beach Resort features a private beach, a marina, and 2 outdoor pools. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Other amenities at this beach hotel include free WiFi in public areas, coffee/tea in a common area, and free use of bicycles.

On private beach

Pool

Free Cancellation

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1.88 mi from city center

$286 nightly

$322 total

Apr 21 - Apr 22

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

Free Cancellation

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0.23 mi from city center

$396 nightly

$446 total

May 3 - May 4

Total with taxes and fees

Guests of Islander Resort have access to a private beach, 2 outdoor pools, and a 24-hour gym. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, tours or tickets, 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 hotel include free WiFi in public areas, meeting rooms, and a conference center.

On private beach

Pool

Free Cancellation

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1.52 mi from city center

$273 nightly

$308 total

Apr 14 - Apr 15

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 water dispenser, and a picnic area.

On private beach

Pool

0.82 mi from city center

$172 nightly

$194 total

May 5 - May 6

Total with taxes and fees

Guests of Hadley Resort and Marina have access to a private beach, a marina, and an outdoor pool. If you drive, put free parking to good use. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Other amenities at this beach hotel include free WiFi in public areas, free use of bicycles, and express check-out.

On private beach

Pool

Free Cancellation

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0.39 mi from city center

$207 nightly

$233 total

May 3 - May 4

Total with taxes and fees

Guests of Sunset Inn enjoy features like an outdoor pool, free WiFi in public areas, and free use of bicycles. A stay here includes free parking. Front-desk staff can assist with securing valuables and luggage storage. Additional amenities include a garden, barbecue grills, and a picnic area.

Pool

Pet friendly

Free Cancellation

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1.82 mi from city center

$233 nightly

$262 total

Apr 12 - Apr 13

Total with taxes and fees

Guests staying at Breezy Palms Resort enjoy access to a marina, an outdoor pool, and free WiFi in public areas. Self parking is available for USD 30.00 per day. Helpful staff can provide tour or ticket assistance, luggage storage, and a safe deposit box at the front desk. Other amenities at this beach aparthotel include a terrace, laundry facilities, and a gift shop.

Pool

Kitchen

0.5 mi from city center

$224 nightly

$252 total

Apr 12 - Apr 13

Total with taxes and fees

Guests staying at La Jolla Resort enjoy access to a private beach, an outdoor pool, and free WiFi in public areas. Limited parking is available. The front desk has multilingual staff that can help with concierge services, and offer advice about sights and eateries nearby. Additional amenities include a garden, barbecue grills, and a picnic area.

On private beach

Pool

0.94 mi from city center

$748 nightly

$842 total

Apr 13 - Apr 14

Total with taxes and fees

Guests of The Islands of Islamorada have access to a marina, 2 outdoor pools, and a 24-hour gym. There's free parking if you drive. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Other amenities at this beach villa include free WiFi in public areas, a hot tub, and free use of bicycles.

0.14 mi from city center

Guests staying at The Caribbean Resort enjoy access to a marina, an outdoor pool, and a hot tub. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Other amenities at this family-friendly hotel include free use of bicycles, a terrace, and laundry facilities.

Pool

Hot Tub

Free Cancellation

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17.51 mi from city center

$147 nightly

$166 total

May 6 - May 7

Total with taxes and fees

Guests staying at Waterside Suites & Marina enjoy access to a marina, an outdoor pool, and free WiFi in public areas. Limited parking is available. The 24-hour front desk has staff standing by to help with luggage storage, tours or 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. Additional amenities include free newspapers, a terrace, and laundry facilities.

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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.

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Upper Matecumbe Key hotels essential information

Accommodation	2,826 hotels
Lowest Price	$166
Highest Price	$842
Popular hotels	Cheeca Lodge & Spa, Chesapeake Beach Resort, Amara Cay Resort, Islander Resort, La Siesta Resort & Villas, Hadley Resort and Marina, Sunset Inn, Breezy Palms Resort, La Jolla Resort, The Islands of Islamorada, The Caribbean Resort, Waterside Suites & Marina

Recent Reviews

4/5 Good

"We enjoyed our stay. Amenities were goo"

A verified traveler stayed at Chesapeake Beach Resort

Posted 3 hours ago

5/5 Excellent

"⭐⭐⭐⭐⭐ Perfect Stay – Already Want to Go Back! We had an amazing stay at Islander Resort and honestly didn’t want to leave! From the moment we arrived (even with a late check-in), Angela at the front desk set the tone for the entire trip. She was incredibly welcoming, fun, and went above and beyond—giving us a full tour of the property and even personally driving us to our villa since we had no idea where we were going. She immediately put us in vacation mode, and that level of service continued throughout our stay. We stayed in an oceanfront villa, which was absolutely beautiful. The setup was perfect—one king bedroom separate from the living area, plus a pullout couch that would easily work for kids or teens. The view was stunning, and having a front porch lounge area right on the water made it even better. What really stood out about this resort is how it manages to feel both secluded and social at the same time. There are so many little tucked-away lounging areas where you can relax in peace, but also plenty of space for larger groups to gather and enjoy. It’s perfect whether you’re traveling as a couple, with friends, or with kids. Speaking of kids/teens—the amount of activities available is incredible. There’s truly something for everyone, which made it a great fit for our family. Another unexpected highlight was the golf cart taxi service around the property—such a unique and convenient touch. Plus, using the Freebee app to get around Islamorada made everything so"

A verified traveler stayed at Islander Resort

Posted 15 hours ago