Hotels in Upper Matecumbe Key

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Nov 18 - Nov 19
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Check prices in Upper Matecumbe Key for tonight, Nov 18 - Nov 19
Nov 19 - Nov 20
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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
$173 nightly
The price is $195 total per night
$195 total
Dec 3 - Dec 4
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

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.09 mi from city center
$268 nightly
The price is $302 total per night
$302 total
Dec 1 - Dec 2
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
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
1.88 mi from city center
$207 nightly
The price is $233 total per night
$233 total
Nov 30 - Dec 1
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

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
$312 nightly
The price is $351 total per night
$351 total
Dec 2 - Dec 3
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 tours or tickets, dry cleaning/laundry, and luggage storage. Other amenities at this beach hotel include free WiFi in public areas, meeting rooms, and a conference center.
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
$136 nightly
The price is $153 total per night
$153 total
Dec 10 - Dec 11
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
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy Islamorada FL
1.46 mi from city center
$188 nightly
The price is $212 total per night
$212 total
Dec 8 - Dec 9
Total with 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 concierge services and luggage storage. Other amenities at this beach hotel include free WiFi in public areas, coffee/tea in a common area, and a terrace.
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
1.52 mi from city center
$199 nightly
The price is $224 total per night
$224 total
Nov 30 - Dec 1
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 a water dispenser.
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
$148 nightly
The price is $166 total per night
$166 total
Nov 24 - Nov 25
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 luggage storage and securing valuables. Additional amenities include a garden, barbecue grills, and a picnic area.
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway, Islamorada, FL
0.5 mi from city center
$122 nightly
The price is $138 total per night
$138 total
Dec 8 - Dec 9
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
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
0.94 mi from city center
$651 nightly
The price is $732 total per night
$732 total
Nov 19 - Nov 20
Total with 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, a garden, and wedding services.
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
$127 nightly
The price is $142 total per night
$142 total
Nov 20 - Nov 21
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.
Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

3.5 out of 5
81450 Overseas Highway, Islamorada, FL
0.67 mi from city center
$295 nightly
The price is $332 total per night
$332 total
Dec 11 - Dec 12
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.
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Upper Matecumbe Key Hotels

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Upper Matecumbe Key hotels essential information

Accommodation
2,836 hotels
Lowest Price
$138
Highest Price
$732
Popular hotels
Chesapeake Beach Resort, Cheeca Lodge & Spa, Amara Cay Resort, Islander Resort, Hadley Resort and Marina, Pines & Palms Resort, La Siesta Resort & Villas, Sunset Inn, La Jolla Resort, The Islands of Islamorada, Breezy Palms Resort, Bayside Villas by Islander Resort

Recent Reviews

Islander Resort

Islander Resort

5/5 Excellent
"Beautiful facility and grounds, wonderful location for quiet get away. The room was very clean. We really enjoyed sitting by the pool and also lounging on our private patio. Would definitely stay here again if we were in the area. A broom on the patio would be helpful to sweep away any insects."
A verified traveler stayed at Islander Resort
Posted 15 hours ago
Islander Resort

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