Book 2 Star Hotels in Upper Matecumbe Key
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Check prices in Upper Matecumbe Key for tomorrow night, Jun 15 - Jun 16Featured 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
$266 nightly
The price is $299 total per night
$299 total
Jun 15 - Jun 16
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.

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.76 mi from city center
$230 nightly
The price is $258 total per night
$258 total
Jun 18 - Jun 19
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.

Islander Resort
82100 Overseas Highway Islamorada FL
0.23 mi from city center
$316 nightly
The price is $356 total per night
$356 total
Jun 21 - Jun 22
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, concierge services, 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.

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.88 mi from city center
$260 nightly
The price is $292 total per night
$292 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.

La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.52 mi from city center
$241 nightly
The price is $271 total per night
$271 total
Jul 6 - Jul 7
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

Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.82 mi from city center
$175 nightly
The price is $197 total per night
$197 total
Jun 16 - Jun 17
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 concierge services and luggage storage. Other amenities at this beach hotel include free WiFi in public areas, free use of bicycles, and express check-out.

Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.67 mi from city center
$280 nightly
The price is $315 total per night
$315 total
Jun 24 - Jun 25
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.

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
Jun 21 - Jun 22
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 a picnic area, barbecue grills, and a garden.

Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.82 mi from city center
$174 nightly
The price is $196 total per night
$196 total
Jun 17 - Jun 18
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.
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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.
Upper Matecumbe Key hotels essential information
Accommodation | 2,776 hotels |
|---|---|
Lowest Price | $196 |
Highest Price | $356 |
Popular hotels | Cheeca Lodge & Spa, Chesapeake Beach Resort, Islander Resort, Amara Cay Resort, La Siesta Resort & Villas, Hadley Resort and Marina, Bayside Villas by Islander Resort, La Jolla Resort, Breezy Palms Resort |
Recent Reviews

Cheeca Lodge & Spa
4/5 Good
"Property and room are beautiful, up to date and well-maintained. Secluded and calm as well. In-house dining was 6.5/10, concierge attitude was subpar and room service the first night was not good, second room service took an hour and a half ."
A verified traveler stayed at Cheeca Lodge & Spa
Posted 13 hours ago
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