Book 2 Star Hotels in Upper Matecumbe Key
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Check prices in Upper Matecumbe Key for tomorrow night, Apr 25 - Apr 26Featured 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
$312 nightly
The price is $351 total per night
$351 total
May 10 - May 11
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, tours or tickets, and securing valuables. 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
$232 nightly
The price is $261 total per night
$261 total
May 10 - May 11
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

Islander Resort
82100 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.23 mi from city center
$262 nightly
The price is $295 total per night
$295 total
May 17 - May 18
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. 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
$249 nightly
The price is $280 total per night
$280 total
May 18 - May 19
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
$232 nightly
The price is $261 total per night
$261 total
May 13 - May 14
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, wedding services, 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
$164 nightly
The price is $185 total per night
$185 total
May 5 - May 6
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.
On private beach
Pool

La Jolla Resort
82216 Overseas Highway Islamorada FL
0.5 mi from city center
$210 nightly
The price is $236 total per night
$236 total
Apr 28 - Apr 29
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

Sunset Inn
82200 Overseas Hwy Islamorada FL
0.39 mi from city center
$199 nightly
The price is $224 total per night
$224 total
Apr 29 - Apr 30
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 barbecue grills, a picnic area, and a garden.
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
$152 nightly
The price is $171 total per night
$171 total
Apr 26 - Apr 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 a gift shop.
Pool
Kitchen
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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 | 2,807 hotels |
|---|---|
Lowest Price | $171 |
Highest Price | $351 |
Popular hotels | Cheeca Lodge & Spa, Chesapeake Beach Resort, Islander Resort, Amara Cay Resort, La Siesta Resort & Villas, Hadley Resort and Marina, La Jolla Resort, Sunset Inn, Breezy Palms Resort |
Recent Reviews

Chesapeake Beach Resort
4/5 Good
"Great property"
A verified traveler stayed at Chesapeake Beach Resort
Posted 9 hours ago
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