Holiday Rentals in Upper Matecumbe Key

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Our top choices for Upper Matecumbe Key holiday rentals

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (682 reviews)
"Amazing stay with my son! Close to everything - right in ocean, beach front and large room! Will stay again for sure!"
United States
Paul
The price is €127
includes taxes & fees
27 May - 28 May
Breezy Palms Resort

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (76 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
The price is €605
includes taxes & fees
27 May - 28 May
The Islands of Islamorada

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is €1,783
includes taxes & fees
31 May - 1 Jun
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (71 reviews)
"We really enjoyed our stay here .. the place was clean — had everything we needed… thanks for sharing your place.."
United States
brenda b.
The price is €253
includes taxes & fees
28 May - 29 May
Paradise in Key Largo, FL

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.6 out of 10, Exceptional, (24 reviews)
"What a neat experience, wonderful boat, waking up on the water was beautiful! Kelly was cery responsive to anything we needed!"
United States
Leanne W.
The price is €368
includes taxes & fees
4 Jun - 5 Jun
Island Sanctuary Islamorada

Key Largo Waterfront Oasis: Private Tiki Bar & Boat Dock!

Key Largo Waterfront Oasis: Private Tiki Bar & Boat Dock!
Key Largo
9.2 out of 10, Wonderful, (25 reviews)
"Ramses was very nice and assisted with what we needed. The property is in a great spot to take your boat. We would like to return one day. Had a nice time"
United States
Cassandra J.
The price is €329
includes taxes & fees
26 May - 27 May
Key Largo Waterfront Oasis: Private Tiki Bar & Boat Dock!

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.0 out of 10, Wonderful, (2 reviews)
"La propiedad me encantó se las recomiendo 100/100%"
United States
Marta
The price is €186
includes taxes & fees
26 May - 27 May
Caloosa Cove Resort by CoolVacay

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Very nice small resort."
United States
Dan
The price is €284
includes taxes & fees
7 Jun - 8 Jun
Island Bay Resort

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
10.0 out of 10, Exceptional, (19 reviews)
"Perfect Stay."
United States
suhaela s.
The price is €387
includes taxes & fees
25 May - 26 May
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (37 reviews)
"Comfortable and well thought out space."
United States
Jessica E.
The price is €354
includes taxes & fees
25 May - 26 May
Charming Home in Key Largo

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Tavernier
10.0 out of 10, Exceptional, (8 reviews)
"Great location and clean"
United States
Matthew H.
The price is €416
includes taxes & fees
9 Jun - 10 Jun
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
10.0 out of 10, Exceptional, (38 reviews)
"We enjoyed our stay. It was very convenient to where we needed to be. The apartment was well stocked and had a nice view. The beds were very comfortable as well and the host was very responsive! Would recommend staying here if you’re in the area. "
United States
Mark F.
The price is €391
includes taxes & fees
25 May - 26 May
Serene Oceanfront Keys Condo

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (114 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is €377
includes taxes & fees
25 May - 26 May
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (48 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is €342
includes taxes & fees
1 Jun - 2 Jun
Amazing Ocean view condo

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Tavernier
9.0 out of 10, Wonderful, (97 reviews)
"Right in the heart of Key Largo but just off the beaten path. Clean, comfortable and cozy. The property has a beach, pool and restaurant which was convenient after a long day of travel."
United States
jodi
The price is €287
includes taxes & fees
26 May - 27 May
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (29 reviews)
"Beautiful condo with nice decor. We enjoyed the pool and was nice having a restaurant on site. I would definitely stay there again "
United States
Cathy
The price is €377
includes taxes & fees
1 Jun - 2 Jun
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (47 reviews)
"There was no staff but the apartment was spotless and very well appointed with amenities like coffee, etc. Everything was clean, neat and new feeling. The beds were very comfortable and the apartment was spacious and welcoming with great views."
United States
Sandra
The price is €377
includes taxes & fees
26 May - 27 May
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (167 reviews)
"Condo was beautiful would definitely stay here again."
United States
Dan M.
The price is €383
includes taxes & fees
31 May - 1 Jun
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Nauti Hideaway Ocean Pointe 2314

Nauti Hideaway Ocean Pointe 2314
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"Great communication. Very clean. We loved view from the room. We would definitely stay here again!"
United States
Cynthia L.
The price is €377
includes taxes & fees
25 May - 26 May
Nauti Hideaway Ocean Pointe 2314

OP-2 Ocean View w/heated pool beach marina

OP-2 Ocean View w/heated pool beach marina
Tavernier
8.4 out of 10, Very good, (11 reviews)
"Great location, thoughtful set-up. "
United States
Michelle J.
The price is €282
includes taxes & fees
23 Jun - 24 Jun
OP-2 Ocean View w/heated pool beach marina
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

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, apart-hotels, 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 €127 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.