Hotels in Upper Matecumbe Key

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Aug 8 - Aug 9
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Top Rated Upper Matecumbe Key Hotels

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
1.76 mi from city center
$201 nightly
The price is $226 total per night
$226 total
Aug 12 - Aug 13
Total includes 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

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
0.09 mi from city center
$259 nightly
The price is $291 total per night
$291 total
Aug 12 - Aug 13
Total includes 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, concierge services, 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
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
1.88 mi from city center
$246 nightly
The price is $276 total per night
$276 total
Sep 1 - Sep 2
Total includes 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

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
0.33 mi from city center
$268 nightly
The price is $302 total per night
$302 total
Aug 14 - Aug 15
Total includes taxes and fees
Guests of Islander Resort have access to a private beach, 2 outdoor pools, and a gym. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to assist with luggage storage, dry cleaning/laundry, and concierge services. 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

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
1.52 mi from city center
$223 nightly
The price is $251 total per night
$251 total
Sep 2 - Sep 3
Total includes 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. 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, wedding services, and a picnic area.
On private beach
Pool
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
0.82 mi from city center
$153 nightly
The price is $172 total per night
$172 total
Aug 17 - Aug 18
Total includes 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.
On private beach
Pool
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
0.94 mi from city center
$599 nightly
The price is $674 total per night
$674 total
Aug 10 - Aug 11
Total includes taxes and fees
Guests staying at The Islands of Islamorada enjoy access to 2 outdoor pools, a 24-hour gym, and free WiFi in public areas. 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 a hot tub, barbecue grills, and wedding services.
Pool
Hot Tub
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway, Islamorada, FL
0.5 mi from city center
$134 nightly
The price is $151 total per night
$151 total
Aug 14 - Aug 15
Total includes 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 picnic area, a garden, and barbecue grills.
On private beach
Pool
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
0.39 mi from city center
$134 nightly
The price is $151 total per night
$151 total
Aug 26 - Aug 27
Total includes 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 luggage storage and securing valuables. Additional amenities include a garden, barbecue grills, and a picnic area.
Pool
Pet friendly
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy, Islamorada, FL
1.46 mi from city center
$228 nightly
The price is $257 total per night
$257 total
Aug 17 - Aug 18
Total includes taxes and fees
Guests of Pines & Palms Resort have access to a private beach, a marina, and an outdoor pool. You can take advantage of free parking, along with limo/town car service. 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, coffee/tea in a common area, and a terrace.
On private beach
Pool
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
1.81 mi from city center
$133 nightly
The price is $148 total per night
$148 total
Sep 7 - Sep 8
Total includes 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 picnic area.
Pool
Kitchen
Islander Bayside Villas and Boatslips

Islander Bayside Villas and Boatslips

3.5 out of 5
81450 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
0.67 mi from city center
$276 nightly
The price is $311 total per night
$311 total
Aug 17 - Aug 18
Total includes taxes and fees
Guests of Islander Bayside Villas and Boatslips 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 barbecue grills and a picnic area.
Pool
Pet friendly
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Upper Matecumbe Key hotels essential information

Accommodation
2,764 hotels
Lowest Price
$148
Highest Price
$674
Popular hotels
Chesapeake Beach Resort, Cheeca Lodge & Spa, Amara Cay Resort, Islander Resort, La Siesta Resort & Villas, Hadley Resort and Marina, The Islands of Islamorada, La Jolla Resort, Sunset Inn, Pines & Palms Resort, Breezy Palms Resort, Islander Bayside Villas and Boatslips

Recent Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

5/5 Excellent
"Great resort with lots to do on-site, pool/kayak/paddle boards/chess/checkers. Morning omelette was delicious & breakfast with the iguanas was fun! Great spot if you’re traveling through or on a fishing trip."
A verified traveler stayed at Chesapeake Beach Resort
Posted 3 days ago
Chesapeake Beach Resort

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