Book 2 Star Hotels in Upper Matecumbe Key
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Upper Matecumbe Key 2 Stars Hotels

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.76 mi from city center
$214 nightly
The price is $241 total per night
$241 total
Jan 6 - Jan 7
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
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.09 mi from city center
$367 nightly
The price is $413 total per night
$413 total
Jan 11 - Jan 12
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 concierge services, securing valuables, and luggage storage. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
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
$277 nightly
The price is $312 total per night
$312 total
Jan 8 - Jan 9
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

Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Free Cancellation
0.82 mi from city center
$178 nightly
The price is $200 total per night
$200 total
Jan 11 - Jan 12
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 luggage storage and tours/tickets. Other amenities at this beach hotel include free WiFi in public areas, free use of bicycles, and express check-out.
On private beach
Pool

Islander Resort
82100 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.33 mi from city center
$326 nightly
The price is $367 total per night
$367 total
Jan 11 - Jan 12
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 concierge services, luggage storage, and dry cleaning/laundry. 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
$248 nightly
The price is $280 total per night
$280 total
Jan 7 - Jan 8
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
82200 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.39 mi from city center
$164 nightly
The price is $185 total per night
$185 total
Jan 19 - Jan 20
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, a picnic area, and barbecue grills.
Pool
Pet friendly

La Jolla Resort
82216 Overseas Highway Islamorada FL
0.5 mi from city center
$154 nightly
The price is $173 total per night
$173 total
Jan 8 - Jan 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 concierge services, 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
82779 Old Hwy Islamorada FL
0.94 mi from city center
$658 nightly
The price is $740 total per night
$740 total
Jan 6 - Jan 7
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 concierge services, and provide local restaurant recommendations. Other amenities at this beach villa include a hot tub, wedding services, and a garden.
Pool
Hot Tub
Don't see what you're looking for?
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 | 2,808 hotels |
|---|---|
Lowest Price | $173 |
Highest Price | $740 |
Popular hotels | Chesapeake Beach Resort, Cheeca Lodge & Spa, Amara Cay Resort, Hadley Resort and Marina, Islander Resort, La Siesta Resort & Villas, Sunset Inn, La Jolla Resort, The Islands of Islamorada |
Recent Reviews

Cheeca Lodge & Spa
5/5 Excellent
"Fantastic resort, will definitely be heading back!"
A verified traveler stayed at Cheeca Lodge & Spa
Posted 13 hours ago
More to Explore
- 5 Star Hotels in Tingler Island
- 5 Star Hotels in Key Largo Park
- 5 Star Hotels in Lower Matecumbe Key
- Hotels near Matecumbe United Methodist Church
- 3 Star Hotels in Bahia Honda Key
- 5 Star Hotels in Bahia Honda Key
- Hotels near Florida Keys Brewing Co.
- 3 Star Hotels in Tavernier
- 4 Star Hotels in Tavernier
- 3 Star Hotels in Duck Key
- 4 Star Hotels in Duck Key
- 5 Star Hotels in Duck Key
- 3 Star Hotels in Florida City
- 5 Star Hotels in Florida City
- Hotels near Hurricane Monument
- 3 Star Hotels in Marathon
- 4 Star Hotels in Marathon
- 4 Star Hotels in Long Key
- 2 Star Hotels in Rock Harbor
- 5 Star Hotels in Rock Harbor
- 5 Star Hotels in Coral Lagoon
- 5 Star Hotels in Plantation Key
- 3 Star Hotels in North Key Largo
- 4 Star Hotels in North Key Largo
- 5 Star Hotels in North Key Largo
- 5 Star Hotels in Homestead
- 4 Star Hotels in Conch Key
- 5 Star Hotels in Conch Key
- 3 Star Hotels in Islamorada
- 4 Star Hotels in Islamorada
- 5 Star Hotels in Islamorada
- Apartments in Islamorada
- Condo Rentals in Islamorada
- Cottages in Islamorada
- Extended Stay Hotels in Islamorada
- Guest Houses in Islamorada
- Beach Resorts & in Islamorada
- Cheap Hotels in Islamorada
- Kid Friendly Hotels in Islamorada
- Gay Friendly Hotels in Islamorada
- Golf Resorts & in Islamorada
- Historic Hotels in Islamorada
- Hotels with Pool in Islamorada
- Hotels with WiFi in Islamorada
- Hotels with Bar in Islamorada
- Hotels with Childcare in Islamorada
- Hotels with Free Breakfast in Islamorada
- Hotels with Free Parking in Islamorada
- Hotels with Hot Tubs in Islamorada
- Hotels with Kitchenettes in Islamorada
- Hotels with Room Service in Islamorada
- Hotels with Tennis Courts in Islamorada
- Luxury Hotels in Islamorada
- Oceanfront Hotels in Islamorada
- Pet Friendly Hotels in Islamorada
- Romantic Getaways & Hotels in Islamorada
- Hotels with Shopping in Islamorada
- Spa Resorts & in Islamorada
- Islamorada Hotels
- Houseboats in Islamorada
- Inns in Islamorada
- Motels in Islamorada
- Vacation Homes in Islamorada
- Rv Parks in Islamorada
- Resorts in Islamorada
- Villas in Islamorada
- 4 Star Hotels in Key Largo
- 4 Star Hotels in Key Colony Beach
- Flights to Miami
- Flights to Islamorada
- Flights from Islamorada
- Flights from Austin to Islamorada
- Flights from Charlotte to Islamorada
- Flights from Chicago to Islamorada
- Flights from Cleveland to Islamorada
- Flights from Denver to Islamorada
- Flights from Detroit to Islamorada
- Flights from Houston to Islamorada
- Flights from Indianapolis to Islamorada
- Flights from Los Angeles to Islamorada
- Flights from Memphis to Islamorada
- Flights from Mexico City to Islamorada
- Flights from Minneapolis - St. Paul to Islamorada
- Flights from New Orleans to Islamorada
- Flights from New York to Islamorada
- Flights from Philadelphia to Islamorada
- Flights from Raleigh to Islamorada
- Flights from Washington to Islamorada
- Flights from Providence to Islamorada
- Flights from Pittsburgh to Islamorada
- Flights from Newark to Islamorada
- Flights from Richmond to Islamorada
- Flights from Halifax to Islamorada
- Flights from Covington to Islamorada
- Beach Hotels in Islamorada
- Luxury Hotels in Islamorada
- Pet-friendly Hotels in Islamorada
- Islamorada vacations
- Islamorada vacation rentals
- Flights to Islamorada
- Cheap Hotels in Islamorada
- Resorts in Islamorada
- Motels in Islamorada
- Cottages in Islamorada
- Houseboats in Islamorada
- Hotels in Islamorada
- Oceanfront Hotels in Islamorada


