Upper Matecumbe Key Holiday Rentals

  • 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 rentals

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (70 reviews)
"Amazing stay, can’t wait to stay there again!"
United States
Anonymous traveller
The price is NZ$1,763
includes taxes & fees
26 Feb - 27 Feb
The Islands of Islamorada

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (618 reviews)
"Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need. "
United States
Alexander
The price is NZ$467
includes taxes & fees
25 Feb - 26 Feb
Breezy Palms Resort

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is NZ$1,936
includes taxes & fees
22 Feb - 23 Feb
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Matecumbe
The price is NZ$1,936
includes taxes & fees
23 Feb - 24 Feb
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
The price is NZ$2,904
includes taxes & fees
23 Feb - 24 Feb
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is NZ$3,283
includes taxes & fees
19 Feb - 20 Feb
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Matecumbe
The price is NZ$3,301
includes taxes & fees
19 Feb - 20 Feb
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
The price is NZ$3,867
includes taxes & fees
24 Feb - 25 Feb
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Charming Suite @Islamorada With Pool Access - Twilight Suite

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
The price is NZ$3,871
includes taxes & fees
23 Feb - 24 Feb
Charming Suite @Islamorada With Pool Access - Twilight Suite

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Matecumbe
The price is NZ$3,676
includes taxes & fees
23 Feb - 24 Feb
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Matecumbe
The price is NZ$5,807
includes taxes & fees
23 Feb - 24 Feb
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (129 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
Treasure Harbor

Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
10.0 out of 10, Exceptional, (1 review)
The price is NZ$1,711
includes taxes & fees
17 Feb - 18 Feb
Premium Floating Bungalow by Stay Ombi

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"An amazing place to switch gears. Great host. Win/win."
United States
Alex Z.
The price is NZ$687
includes taxes & fees
15 Feb - 16 Feb
Island Sanctuary Islamorada

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (44 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is NZ$749
includes taxes & fees
1 Mar - 2 Mar
Amazing Ocean view condo

3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (152 reviews)
"Great stay lovely home "
United States
Yezenia
The price is NZ$839
includes taxes & fees
4 Mar - 5 Mar
3212 Across from Pool * King & Queen/Twin Bunk Bed

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (26 reviews)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is NZ$910
includes taxes & fees
11 Mar - 12 Mar
Lazy Daze Double King Suite Ocean Pointe 2310

Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View
Tavernier
10.0 out of 10, Exceptional, (108 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is NZ$904
includes taxes & fees
10 Mar - 11 Mar
Serenity In The Sun Condo Fabulous Ocean View

Spacious 4BR/3BA • 8 Beds • Mariner’s Club Community • Perfect for Large Groups

Spacious 4BR/3BA • 8 Beds • Mariner’s Club Community • Perfect for Large Groups
Rock Harbor
10.0 out of 10, Exceptional, (72 reviews)
"Well organized, clean, beds and pillows were very comfortable, quit and very relaxing.If you are looking for a place to stay while diving, I would highly recommend staying here."
United States
Tracy M.
The price is NZ$2,030
includes taxes & fees
13 Mar - 14 Mar
Spacious 4BR/3BA • 8 Beds • Mariner’s Club Community • Perfect for Large Groups

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, (106 reviews)
"Loved the location, the decor and the pool area!"
United States
Laureen h.
The price is NZ$2,551
includes taxes & fees
28 Feb - 1 Mar
NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES
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

Everything you need to know about Upper Matecumbe Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upper Matecumbe Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upper Matecumbe Key holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Upper Matecumbe Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upper Matecumbe Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upper Matecumbe Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upper Matecumbe Key holiday rentals we have selected for you start as low as NZ$467 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Upper Matecumbe Key rentals

At Expedia, we put the best Upper Matecumbe Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Upper Matecumbe Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upper Matecumbe Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upper Matecumbe Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.