Hotels in Upper Matecumbe Key
Search over 2,789 hotels from $308
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
Tomorrow night
Check prices in Upper Matecumbe Key for tomorrow night, Feb 21 - Feb 22Top Rated Upper Matecumbe Key Hotels

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.76 mi from city center
$373 nightly
The price is $420 total per night
$420 total
Mar 22 - Mar 23
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
$432 nightly
The price is $487 total per night
$487 total
Mar 3 - Mar 4
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 luggage storage, dry cleaning/laundry, and concierge services. 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
$395 nightly
The price is $445 total per night
$445 total
Mar 1 - Mar 2
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
$492 nightly
The price is $553 total per night
$553 total
Feb 24 - Feb 25
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

Islander Resort
82100 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.23 mi from city center
$429 nightly
The price is $483 total per night
$483 total
Mar 23 - Mar 24
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, luggage storage, 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

Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.82 mi from city center
$307 nightly
The price is $346 total per night
$346 total
Mar 1 - Mar 2
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 concierge services. Other amenities at this beach hotel include free WiFi in public areas, free use of bicycles, and express check-out.
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
$287 nightly
The price is $323 total per night
$323 total
Mar 19 - Mar 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
$274 nightly
The price is $308 total per night
$308 total
Mar 1 - Mar 2
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
82779 Old Hwy Islamorada FL
0.94 mi from city center
$948 nightly
The price is $1,067 total per night
$1,067 total
Feb 26 - Feb 27
Total with taxes and fees
Guests of The Islands of Islamorada have access to a marina, 2 outdoor pools, and a 24-hour gym. 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 free WiFi in public areas, a hot tub, and free use of bicycles.
Pool
Hot Tub

Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.82 mi from city center
$290 nightly
The price is $326 total per night
$326 total
Mar 17 - Mar 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 a picnic area.
Pool
Kitchen

Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.67 mi from city center
$541 nightly
The price is $609 total per night
$609 total
Feb 22 - Feb 23
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.
Pool
Pet friendly

Pines & Palms Resort
80401 Old Hwy Islamorada FL
1.46 mi from city center
$538 nightly
The price is $605 total per night
$605 total
Feb 23 - Feb 24
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 tours/tickets and luggage storage. 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
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.
How much is a Upper Matecumbe Key hotel?
Check Upper Matecumbe Key hotel room prices by star rating

5 Star Hotels
3 properties
Upper Matecumbe Key hotels essential information
Accommodation | 2,789 hotels |
|---|---|
Lowest Price | $308 |
Highest Price | $1,067 |
Popular hotels | Chesapeake Beach Resort, Cheeca Lodge & Spa, Amara Cay Resort, La Siesta Resort & Villas, Islander Resort, Hadley Resort and Marina, Sunset Inn, La Jolla Resort, The Islands of Islamorada, Breezy Palms Resort, Bayside Villas by Islander Resort, Pines & Palms Resort |
Recent Reviews

Islander Resort
5/5 Excellent
"Very nice accommodations. Helpful and polite staff. Many amenities. Beautiful ocean views and sunrises. Would absolutely stay there again."
A verified traveler stayed at Islander Resort
Posted 4 days ago
More to Explore
More to Explore
- Hotels near Windley Key Fossil Reef Geological State Park
- Hotels near Hurricane Monument
- Hotels near Pigeon Key
- Hotels near Florida Keys Dive Center
- Hotels near MarineLab Undersea Laboratory
- Hotels near Anne's Beach
- Anglers Park Hotels
- Hotels near Bluefin Rock Harbor Marina
- Hotels near Caribbean Club Bar
- Matecumbe Hotels
- Long Key Hotels
- Hotels near Jacob's Aquatic Center
- Conch Key Hotels
- Hotels near Long Key State Park
- Hotels near Florida Keys Brewing Co.
- Hotels near Bud n' Mary's Dive Center
- Indian Waterways Hotels
- Hotels near Islamorada County Park
- Key Largo Village Hotels
- Lignumvitae Key Botanical State Park Hotels
- Duck Key Hotels
- Hotels near Sunset Drive Beach
- 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
- Hotels with a Wedding Venue 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
- Hotels near Founders Park
- Hotels near Jimmy Johnson's Big Chill
- Hotels near Harry Harris Park
- Key Largo Hotels
- Hotels near Fiesta Key
- Hotels near Matecumbe United Methodist Church
- Tavernier Hotels
- 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
- Motels in Islamorada
- Flights to Islamorada
- Oceanfront Hotels in Islamorada
- Islamorada vacations
- Islamorada vacation rentals
- Cheap Hotels in Islamorada
- Beach Hotels in Islamorada
- Resorts in Islamorada
- Houseboats in Islamorada
- Pet-friendly Hotels in Islamorada
- Cottages in Islamorada
- Luxury Hotels in Islamorada
- Hotels in Islamorada






