Holiday Homes in Upper Matecumbe Key

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Upper Matecumbe Key holiday homes

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

1. Little Peace of Haven

Little Peace of Haven
Key Largo
9.0 out of 10, Wonderful, (6 reviews)
"Lovely clean, quiet, perfect location for exploring the upper keys! An fantastic value!"
United States
Mitchel R.
The price is AU$574
includes taxes & fees
1 Dec - 2 Dec
Little Peace of Haven
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a yellow tablecloth.

2. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is AU$502
includes taxes & fees
15 Nov - 16 Nov
Charming Home in Key Largo
A wooden deck with yellow chairs, a pool, and a building with a covered area.

3. Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.6 out of 10, Exceptional, (54 reviews)
"We had a nice stay"
United States
Kevin M.
The price is AU$414
includes taxes & fees
11 Nov - 12 Nov
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
A deck with outdoor seating and a view of the water.

4. Waterfront 3BR Retreat: Pool, Spa & Kayaks

Waterfront 3BR Retreat: Pool, Spa & Kayaks
Key Largo
The price is AU$1,122
includes taxes & fees
1 Dec - 2 Dec
Waterfront 3BR Retreat: Pool, Spa & Kayaks
A bedroom with a large bed, a desk, and a chair, a mirror, and decorative wall art.

5. Serenity Bungalow at Largo Resort

Serenity Bungalow at Largo Resort
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
" We regret that we only booked for one night. We will definitely return for a longer stay. Everything about Key Largo Resort was perfect! The setting, the location, the accommodations, everything! Thank you for an amazing experience! We will be back! "
United States
Kimberly V.
The price is AU$589
includes taxes & fees
11 Nov - 12 Nov
Serenity Bungalow at Largo Resort
A table with a glass of beverage, a mug, and a plate with food, overlooking a pool with boats and palm trees under a sunset sky.

6. 4. Cozy Key Largo Waterfront Studio | Dive

4. Cozy Key Largo Waterfront Studio | Dive
Key Largo
9.8 out of 10, Exceptional, (13 reviews)
"Excellent stay, as always!"
United States
Monica G.
4. Cozy Key Largo Waterfront Studio | Dive
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

7. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (77 reviews)
"Great place!"
United States
Jessica S.
The price is AU$1,106
includes taxes & fees
11 Nov - 12 Nov
Sunrise Escape - Ocean Front Villa - Sleeps 10
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

8. New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
Key Largo
9.2 out of 10, Wonderful, (24 reviews)
"The lagoon was beautiful and fun."
United States
Teresa H.
The price is AU$605
includes taxes & fees
11 Nov - 12 Nov
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
A beachside wooden deck with Adirondack chairs, a thatched-roof gazebo, and a grill.

9. Key Largo Villa, Kawama P6, 3/3

Key Largo Villa, Kawama P6, 3/3
Key Largo
9.8 out of 10, Exceptional, (152 reviews)
"The property was very nice, we recommend it."
United States
Gaby
The price is AU$859
includes taxes & fees
17 Nov - 18 Nov
Key Largo Villa, Kawama P6, 3/3
A modern kitchen with a large island, stainless steel appliances, and a view of the water.

10. New Oceanside Paradise with Pool and Waterfront Views!

New Oceanside Paradise with Pool and Waterfront Views!
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great "
United States
Ravone L.
The price is AU$1,365
includes taxes & fees
15 Nov - 16 Nov
New Oceanside Paradise with Pool and Waterfront Views!
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

11. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
10.0 out of 10, Exceptional, (1 review)
"Great property. Highly recommend."
United States
Karl B.
The price is AU$1,336
includes taxes & fees
12 Nov - 13 Nov
Oceanside Retreat w/Rooftop, Pool & Kayaks
A bedroom with a large bed, a desk with a chair, a mirror, and a wall-mounted artwork.

12. Tranquility Bungalow at Largo Resort

Tranquility Bungalow at Largo Resort
Key Largo
9.4 out of 10, Exceptional, (9 reviews)
"Very Zen atmosphere. Alex and the rest of the staff very friendly and welcoming. "
United States
Becky M.
The price is AU$643
includes taxes & fees
15 Nov - 16 Nov
Tranquility Bungalow at Largo Resort
A beachside wooden deck with Adirondack chairs, a thatched-roof gazebo, and a grill.

13. Key Largo Villa, Kawama K5, 3/3

Key Largo Villa, Kawama K5, 3/3
Key Largo
10.0 out of 10, Exceptional, (68 reviews)
"Lovely location and nice kitchen."
United States
Susan S.
The price is AU$809
includes taxes & fees
11 Nov - 12 Nov
Key Largo Villa, Kawama K5, 3/3
A round table set for two with a view of the ocean and palm trees.

14. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (24 reviews)
"Perfect rental, can’t say enough about it. The host was fantastic. Would definitely stay here again."
United States
Tammy C.
The price is AU$676
includes taxes & fees
18 Nov - 19 Nov
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
A large swimming pool surrounded by palm trees and a beach, with a building in the background.

15. Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more

Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
Rock Harbor
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful property Great location Gorgeous pool and great facilities available Perfect stay"
United Kingdom
Jennifer
The price is AU$1,457
includes taxes & fees
19 Nov - 20 Nov
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
A bedroom with a large bed, a desk, and a mirror.

16. Sunset Bay View Bungalow at Largo Resort

Sunset Bay View Bungalow at Largo Resort
Key Largo
9.0 out of 10, Wonderful, (2 reviews)
"We got everything we need, a relaxing place, great service, easy to find, restaurants all over the place and most important of all very clean and beautiful. We loved."
United States
Ricardo M.
The price is AU$621
includes taxes & fees
11 Nov - 12 Nov
Sunset Bay View Bungalow at Largo Resort
A room with a grey sofa, a chair, a lamp, and large windows with a view of palm trees and a building outside.

17. Key Largo Tiny House, Marina, Beach + Pool Access

Key Largo Tiny House, Marina, Beach + Pool Access
Key Largo
10.0 out of 10, Exceptional, (1 review)
"Everything was great, especially The Newman Hospitality Company who I dealt with. Great customer service!"
United States
Brittany C.
The price is AU$465
includes taxes & fees
11 Nov - 12 Nov
Key Largo Tiny House, Marina, Beach + Pool Access
An aerial view of a resort with multiple buildings, a central pool area, and a beach.

18. NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (63 reviews)
"Great house and even better location!"
United States
Sofia C.
The price is AU$851
includes taxes & fees
11 Nov - 12 Nov
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
A wooden deck with lounge chairs, a pool, and a dock with boats.

19. Waterfront Tiny House w Pool, Beach, and Boat Dock

Waterfront Tiny House w Pool, Beach, and Boat Dock
Key Largo
9.6 out of 10, Exceptional, (70 reviews)
"We were really impressed with the house - it had all the little things that made the stay so comfortable - reclining chairs in the living room, A/C in every room, a great outside deck complete with a big TV and clean, clean, clean."
United States
Ann
The price is AU$558
includes taxes & fees
17 Nov - 18 Nov
Waterfront Tiny House w Pool, Beach, and Boat Dock
Open kitchen

20. Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (184 reviews)
"Great place to stay"
United States
Eric B.
The price is AU$985
includes taxes & fees
15 Nov - 16 Nov
Oceanside Kawama Villa R5
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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Learn more about Upper Matecumbe Key

Venture to sights like Bud n' Mary's Dive Center and Florida Keys Brewing Co. as you discover Upper Matecumbe Key.

See all hotels in Upper Matecumbe Key
A shark sculpture with a sign above it that reads "Islamorada Florida Keys".

Top reviews in Upper Matecumbe Key

A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe

10/10 Excellent

Idyllic beautiful beach setting, clean comfortable rooms, lovely setting.
Australia
Yuli
Reviewed December 14, 2025
Chesapeake Beach Resort

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