Holiday Homes in Upper Matecumbe Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Upper Matecumbe Key holiday homes

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (32 reviews)
"Clean, updated, had everything we could have asked for. "
United States
Debra D.
The price is AU$595
includes taxes & fees
29 Mar - 30 Mar
Charming Home in Key Largo

Waterfront Pool, Beach, Dock, Kayaks

Waterfront Pool, Beach, Dock, Kayaks
Key Largo
9.6 out of 10, Exceptional, (83 reviews)
"Beautiful deck right on the water."
United States
Laura
The price is AU$825
includes taxes & fees
13 Apr - 14 Apr
Waterfront Pool, Beach, Dock, Kayaks

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.4 out of 10, Exceptional, (91 reviews)
"Everything was great!"
United States
Bethany B.
The price is AU$704
includes taxes & fees
13 Apr - 14 Apr
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Casa Largo

Casa Largo
Key Largo
9.2 out of 10, Wonderful, (131 reviews)
"Very nice updated home in a nice community with views to the lagoon. Would definitely stay here again!"
United States
Priscilla G.
The price is AU$1,032
includes taxes & fees
23 Mar - 24 Mar
Casa Largo

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
9.4 out of 10, Exceptional, (62 reviews)
"Nice location with 5 min walk to ocean view. "
United States
Trevor P.
The price is AU$1,058
includes taxes & fees
10 Apr - 11 Apr
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Key Largo
9.8 out of 10, Exceptional, (172 reviews)
"Loved this place and will stay again if we go back to the Keys. Gated community with golf cart to go to the pier with great community resources, grills and sitting areas. Favorite part was the lagoon in the middle of the community not far from the screened in back porch. Full of fish you can swim with and calm beach area that is clean and nice with shade when you need it. We didn’t want to leave this place. Highly recommend!!"
United States
Chandler G.
The price is AU$1,613
includes taxes & fees
18 Mar - 19 Mar
NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (68 reviews)
"Great place!"
United States
Jessica S.
The price is AU$1,384
includes taxes & fees
17 Mar - 18 Mar
Sunrise Escape - Ocean Front Villa - Sleeps 10

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, (50 reviews)
"super nice and modern house, really lovely host, the kitchen is equipped with all you need for cookingall decoration is so nice fits to the beach feelingall rooms are modern and nice decoratedwe could just recommend ! if we will come back to Florida this will be again our choice!"
United States
Anonymous traveller
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

Oceanfront Tiny Villa in the Heart of the FL Keys

Oceanfront Tiny Villa in the Heart of the FL Keys
Marathon
10.0 out of 10, Exceptional, (13 reviews)
"Great place, beautiful view, close to everything."
United States
Maria G.
Oceanfront Tiny Villa in the Heart of the FL Keys

SPECIAL-2 Bed 2.5 Bath Villa including Cabana Club membership

SPECIAL-2 Bed 2.5 Bath Villa including Cabana Club membership
Marathon
9.8 out of 10, Exceptional, (146 reviews)
"Great location and very neat place!"
United States
FERNANDO S.
SPECIAL-2 Bed 2.5 Bath Villa including Cabana Club membership

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (49 reviews)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is AU$943
includes taxes & fees
13 Apr - 14 Apr
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (142 reviews)
"The host, house and amenities were perfect. all praises.."
United States
Pete S.
The price is AU$1,284
includes taxes & fees
2 Apr - 3 Apr
Beautiful Kawama Townhouse

Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.

Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.
Key Largo Village
The price is AU$1,919
includes taxes & fees
17 Mar - 18 Mar
Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.

Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (12 reviews)
"This villa exceeded our expectations. All the bedrooms have king size beds and there is a 3/4 bath on the first floor which was unexpected and perfect as all the couples had there own bathroom. Melissa was very fast to respond to some issues (smoke alarm in one of the bedrooms needed batteries) and maintenance was there within the hour. The pool was heated and very private. I would highly recommend this place to stay. "
United States
Melissa B.
The price is AU$970
includes taxes & fees
8 Apr - 9 Apr
Charming 3-bedroom house featuring a heated private pool.

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
9.4 out of 10, Exceptional, (34 reviews)
"Perfect for our get away"
United States
Kelly H.
The price is AU$943
includes taxes & fees
13 Apr - 14 Apr
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES

NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES
Rock Harbor
9.8 out of 10, Exceptional, (107 reviews)
"Loved the location, the decor and the pool area!"
United States
Laureen h.
The price is AU$1,952
includes taxes & fees
17 Mar - 18 Mar
NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES

Enchanted Paradise Bungalow at Largo Resort

Enchanted Paradise Bungalow at Largo Resort
Key Largo
The price is AU$864
includes taxes & fees
12 Apr - 13 Apr
Enchanted Paradise Bungalow at Largo Resort

MODERN VILLA - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - UPSCALE OCEANFRONT RESORT

MODERN VILLA - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - UPSCALE OCEANFRONT RESORT
Rock Harbor
9.6 out of 10, Exceptional, (48 reviews)
"We had an absolutely wonderful experience at this condo. From the moment we arrived, everything was spotless, beautifully decorated, and even better than the listing photos. The space felt warm, inviting, and thoughtfully set up with all the comforts of home.The location was perfect: quiet, safe, and close to everything we needed. Whether we were relaxing inside or exploring the area, it truly felt like the ideal home base."
United States
Tracy D.
The price is AU$1,445
includes taxes & fees
20 Mar - 21 Mar
MODERN VILLA - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - UPSCALE OCEANFRONT RESORT

Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful views. Very nice accommodations. Wonderfull location!"
United States
michael h.
The price is AU$999
includes taxes & fees
8 Apr - 9 Apr
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Key Largo
9.6 out of 10, Exceptional, (126 reviews)
"We had a wonderful time host was responsive and the property was perfect for our needs"
United States
Mike C.
The price is AU$712
includes taxes & fees
13 Apr - 14 Apr
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Upper Matecumbe Key Hotel Reviews

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Holiday Homes information

Number of reviews
1,190
Accommodation
665 Holiday Homes
Lowest Price
AU$595
Highest Price
AU$1,952

Explore a world of travel with Expedia