Search Holiday Homes in Upper Matecumbe Key

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

Browse Select Upper Matecumbe Key Holiday Homes

Angler's Reef Resort by KeysCaribbean
Private beach, sun-loungers

Angler's Reef Resort by KeysCaribbean

3.5 star property
9.0 out of 10, Wonderful, (14)
"House is situated right off the main road and very noisy at all times day and night. Also no blinds in the Master room which is located at back of home off the road. Had to buy a set of frying pans because the pans there were in terrible condition for Teflon coated."
Angler's Reef Resort by KeysCaribbean
Mariner's Club Key Largo by KeysCaribbean
2 outdoor pools, open 10:00 AM to 6:00 PM, pool loungers

Mariner's Club Key Largo by KeysCaribbean

3.5 star property
7.4 out of 10, Good, (263)
"Great property "
Mariner's Club Key Largo by KeysCaribbean
Holly s Hideout in Islamorada
House

Holly s Hideout in Islamorada

2.0 star property
Holly s Hideout in Islamorada
Lime Key in Key Largo
House

Lime Key in Key Largo

2.0 star property
Lime Key in Key Largo
The Caribbean Resort Malayan Palm East
Outdoor pool

The Caribbean Resort Malayan Palm East

3.5 star property
The Caribbean Resort Malayan Palm East
The Caribbean Resort Canary Island Palm South
Outdoor pool

The Caribbean Resort Canary Island Palm South

3.5 star property
The Caribbean Resort Canary Island Palm South
Sunset Beach in Key Largo
House

Sunset Beach in Key Largo

2.0 star property
Sunset Beach in Key Largo
The Caribbean Resort Royal Palm North
Outdoor pool

The Caribbean Resort Royal Palm North

3.5 star property
The Caribbean Resort Royal Palm North
The Caribbean Resort Jamaican Palm House
Outdoor pool

The Caribbean Resort Jamaican Palm House

3.5 star property
The Caribbean Resort Jamaican Palm House
The Caribbean Resort Princess Palm South
Outdoor pool

The Caribbean Resort Princess Palm South

3.5 star property
The Caribbean Resort Princess Palm South
The Caribbean Resort Fish Tail Palm
Outdoor pool

The Caribbean Resort Fish Tail Palm

3.5 star property
The Caribbean Resort Fish Tail Palm
The Caribbean Resort Canary Island Palm North
Outdoor pool

The Caribbean Resort Canary Island Palm North

3.5 star property
The Caribbean Resort Canary Island Palm North
Oleander Hideaway
House | In-room dining

Oleander Hideaway

3.5 star property
Oleander Hideaway
Brand New Key Largo Home
Full-sized fridge, microwave, oven, stovetop

Brand New Key Largo Home

3.5 star property
Brand New Key Largo Home
The Caribbean Resort Bird of Paradise - One Bedroom One Bath
Outdoor pool

The Caribbean Resort Bird of Paradise - One Bedroom One Bath

3.5 star property
The Caribbean Resort Bird of Paradise - One Bedroom One Bath
The Caribbean Resort Coconut Palm North
Outdoor pool

The Caribbean Resort Coconut Palm North

4.0 star property
The Caribbean Resort Coconut Palm North
Serenity by Florida Keys Luxury Rentals
House, 3 Bedrooms | Pool

Serenity by Florida Keys Luxury Rentals

4.0 star property
Serenity by Florida Keys Luxury Rentals
Pineapple Beach by Florida Keys Luxury Rentals
House, 5 Bedrooms | Beach/ocean view

Pineapple Beach by Florida Keys Luxury Rentals

4.0 star property
Pineapple Beach by Florida Keys Luxury Rentals
Lime Key by Florida Keys Luxury Rentals
House, 3 Bedrooms | Balcony

Lime Key by Florida Keys Luxury Rentals

4.0 star property
Lime Key by Florida Keys Luxury Rentals
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"The hotel is wonderful "
Nicholas 2-night trip
Posted 21 hours ago
Chesapeake Beach Resort