Book 2 Star Hotels in Upper Matecumbe Key
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Tomorrow night
Check prices in Upper Matecumbe Key for tomorrow night, Mar 26 - Mar 27Featured Upper Matecumbe Key 2 Stars Hotels

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
$416 nightly
The price is $469 total per night
$469 total
Apr 13 - Apr 14
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

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.76 mi from city center
$273 nightly
The price is $308 total per night
$308 total
Apr 21 - Apr 22
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

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
1.88 mi from city center
$288 nightly
The price is $325 total per night
$325 total
Apr 20 - Apr 21
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

Islander Resort
82100 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.23 mi from city center
$389 nightly
The price is $438 total per night
$438 total
Apr 12 - Apr 13
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

La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.52 mi from city center
$334 nightly
The price is $376 total per night
$376 total
Apr 19 - Apr 20
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

Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.82 mi from city center
$193 nightly
The price is $217 total per night
$217 total
Apr 22 - Apr 23
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

Sunset Inn
82200 Overseas Hwy Islamorada FL
0.39 mi from city center
$222 nightly
The price is $250 total per night
$250 total
Apr 15 - Apr 16
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

Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.82 mi from city center
$257 nightly
The price is $289 total per night
$289 total
Apr 8 - Apr 9
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

La Jolla Resort
82216 Overseas Highway Islamorada FL
0.5 mi from city center
$254 nightly
The price is $286 total per night
$286 total
Mar 30 - Mar 31
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
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See all available properties in Upper Matecumbe Key
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.
Upper Matecumbe Key hotels essential information
Accommodation | 2,809 hotels |
|---|---|
Lowest Price | $217 |
Highest Price | $469 |
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 |
Recent Reviews

Hadley Resort and Marina
5/5 Excellent
"Clean room, great location, friendly staff."
A verified traveler stayed at Hadley Resort and Marina
Posted 11 hours ago
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