Hotels in Upper Matecumbe Key
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Tomorrow night
Check prices in Upper Matecumbe Key for tomorrow night, May 23 - May 24Top Rated Upper Matecumbe Key Hotels

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.76 mi from city center
$234 nightly
The price is $263 total per night
$263 total
Jun 8 - Jun 9
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

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.09 mi from city center
$264 nightly
The price is $297 total per night
$297 total
May 26 - May 27
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 dry cleaning/laundry, securing valuables, and tours or tickets. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
On private beach
Pool

Islander Resort
82100 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.23 mi from city center
$271 nightly
The price is $304 total per night
$304 total
May 31 - Jun 1
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 concierge services, luggage storage, 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 hotel include free WiFi in public areas, meeting rooms, and a conference center.
On private beach
Pool

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.88 mi from city center
$253 nightly
The price is $284 total per night
$284 total
May 26 - May 27
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

La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.52 mi from city center
$237 nightly
The price is $266 total per night
$266 total
May 27 - May 28
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 wedding services.
On private beach
Pool

Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.82 mi from city center
$181 nightly
The price is $204 total per night
$204 total
Jun 21 - Jun 22
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 luggage storage and tours/tickets. Other amenities at this beach hotel include free WiFi in public areas, free use of bicycles, and express check-out.
On private beach
Pool

Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.67 mi from city center
$245 nightly
The price is $275 total per night
$275 total
Jun 1 - Jun 2
Total with taxes and fees
Guests of Bayside Villas by Islander Resort enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. There's free parking and a free area shuttle. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Other amenities at this beach hotel include a picnic area and barbecue grills.
Pool
Pet friendly

La Jolla Resort
82216 Overseas Highway Islamorada FL
0.5 mi from city center
$214 nightly
The price is $241 total per night
$241 total
May 26 - May 27
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 tours or tickets, and offer advice about sights and eateries nearby. Additional amenities include barbecue grills, a picnic area, and a garden.
On private beach
Pool

Breezy Palms Resort
80015 Overseas Highway Islamorada FL
1.82 mi from city center
$122 nightly
The price is $138 total per night
$138 total
May 26 - May 27
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 barbecue grills.
Pool
Kitchen

Sunset Inn
82200 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.39 mi from city center
$189 nightly
The price is $213 total per night
$213 total
Jun 8 - Jun 9
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, a picnic area, and barbecue grills.
Pool
Pet friendly

The Islands of Islamorada
82779 Old Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.94 mi from city center
$624 nightly
The price is $702 total per night
$702 total
May 27 - May 28
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 concierge services, 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.
Pool
Hot Tub

The Caribbean Resort
117 Carroll St Islamorada FL
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
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View all propertiesLowest 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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5 Star Hotels
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Upper Matecumbe Key hotels essential information
Accommodation | 2,816 hotels |
|---|---|
Lowest Price | $138 |
Highest Price | $702 |
Popular hotels | Chesapeake Beach Resort, Cheeca Lodge & Spa, Islander Resort, Amara Cay Resort, La Siesta Resort & Villas, Hadley Resort and Marina, Bayside Villas by Islander Resort, La Jolla Resort, Breezy Palms Resort, Sunset Inn, The Islands of Islamorada, The Caribbean Resort |
Recent Reviews

Amara Cay Resort
1/5 Terrible
"Didn't like the seclusion cleanliness set up"
A verified traveler stayed at Amara Cay Resort
Posted 10 hours ago
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