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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Resort in Upper Matecumbe Key

Cheeca Lodge & Spa
Private beach, sun-loungers, beach umbrellas, beach towels

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1140)
"We absolutely loved our stay at cheeca, will not be our last!"
The price is NZ$587
includes taxes & fees
11 Aug - 12 Aug
Cheeca Lodge & Spa
Baker's Cay Resort Key Largo, Curio Collection by Hilton
32-inch LCD TV with satellite channels, TV, iPod dock

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4.0 star property
8.6 out of 10, Excellent, (1011)
"The resort was beautiful and although it was sold out it never seemed med to crowded. "
The price is NZ$685
includes taxes & fees
14 Aug - 15 Aug
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort
Exterior

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1241)
"Amazing stay"
The price is NZ$420
includes taxes & fees
20 Aug - 21 Aug
Amara Cay Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3 outdoor pools, a heated pool, pool umbrellas, pool loungers

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 star property
9.0 out of 10, Wonderful, (48)
"This place is a gem. It was beautiful and quiet. "
The price is NZ$444
includes taxes & fees
20 Aug - 21 Aug
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Playa Largo Resort & Spa, Autograph Collection
Outdoor pool, pool cabanas (surcharge), pool umbrellas

Playa Largo Resort & Spa, Autograph Collection

4.5 star property
9.0 out of 10, Wonderful, (1005)
"really nice beach "
The price is NZ$585
includes taxes & fees
21 Aug - 22 Aug
Playa Largo Resort & Spa, Autograph Collection
La Siesta Resort & Villas
Outdoor pool, pool loungers

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1005)
"Pool and bar area very nice and fun for our family "
The price is NZ$386
includes taxes & fees
5 Aug - 6 Aug
La Siesta Resort & Villas
Lime Tree Bay Resort
Exterior

Lime Tree Bay Resort

3.5 star property
9.2 out of 10, Wonderful, (1086)
"Great resort! We loved the games and hammocks around the property. Loved how we could ride bikes and paddle board right from the resort. "
Lime Tree Bay Resort
Villas At Hawks Cay Resort
5 outdoor pools, pool cabanas (surcharge), pool umbrellas

Villas At Hawks Cay Resort

4.0 star property
8.6 out of 10, Excellent, (96)
"Family had a great time! Staff was outstanding."
Villas At Hawks Cay Resort
Matecumbe Resort
Private beach, white sand

Matecumbe Resort

2.0 star property
8.8 out of 10, Excellent, (61)
"Beautiful resort! All the amenities were great and it was centrally located."
The price is NZ$278
includes taxes & fees
14 Aug - 15 Aug
Matecumbe Resort
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
Beach

2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

9.0 out of 10, Wonderful, (2)
"We enjoyed our stay here, although units are older and do need some sprucing up.It was nice to have a beach onsite, as well as a heated pool, the use of (older) bikes and kayaks. We were only a few miles from the action of Islamorada, including restaurants, tourist attractions, shopping, breweries"
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
Keys Villa
Property grounds

Keys Villa

10.0 out of 10, Exceptional, (7)
"Wonderful place to stay. It was quiet with a private beach. Just what we were looking for. "
Keys Villa
2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay
Outdoor dining

2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay

2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay
The Best Spot for Your Next Getaway! Terrace w/ Water View, Full Kitchen, Pool
Pool

The Best Spot for Your Next Getaway! Terrace w/ Water View, Full Kitchen, Pool

The Best Spot for Your Next Getaway! Terrace w/ Water View, Full Kitchen, Pool
Beautiful oceanfront resort located at mile marker 73.8
Outdoor pool

Beautiful oceanfront resort located at mile marker 73.8

Beautiful oceanfront resort located at mile marker 73.8
Lowest 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.
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Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"We have been coming here for 5 years and the place gets better and better. Every year we come they have added new amenities. The beach and pools are amazing and the location makes it easy to go anywhere in the Keys quickly. If you are looking for a great resort for a great price in this area it is a GREAT option!"
Michael 4-night trip
Posted 13 hours ago
Chesapeake Beach Resort