A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

Upper Matecumbe Key Vacation Rentals

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Our top choices for Upper Matecumbe Key vacation rentals

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (716 reviews)
"my 2nd time staying here and i will be back for a 3rd"
United States
Tristan
The price is CA $131
CA $220 total
includes taxes & fees
Sep 2 - Sep 3
Breezy Palms Resort

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is CA $2,270
CA $2,876 total
includes taxes & fees
Aug 9 - Aug 10
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

3. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (166 reviews)
"The houseboat were a great experience not only for the kid's but the adults also. Seeing the manatees swim around the cove was awesome! It was a great place to meet your neighbors as the porches are very close. The swimming pool is a great addition to the property! If going back to the area, I would definitely go there again! We really enjoyed our visit there!"
United States
Kelly
The price is CA $175
CA $395 total
includes taxes & fees
Aug 5 - Aug 6
Treasure Harbor

4. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (35 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
The price is CA $126
CA $445 total
includes taxes & fees
Aug 30 - Aug 31
Florida Keys Getaway - Slps 4 - Ocean View

5. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (176 reviews)
"Very pleased with our stay"
United States
Vernon Micheal
The price is CA $359
CA $404 total
includes taxes & fees
Aug 9 - Aug 10
Island Bay Resort

6. Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
10.0 out of 10, Exceptional, (4 reviews)
"Very clean with everything you could need for your time in the Florida keys! The host was very responsive and helpful. Perfect place for a weekend with our dog."
United States
Anonymous traveller
The price is CA $139
CA $417 total
includes taxes & fees
Aug 6 - Aug 7
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

7. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (52 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
The price is CA $189
CA $490 total
includes taxes & fees
Aug 4 - Aug 5
Amazing Ocean view condo

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Everything was wonderful! We enjoyed our stay very much. "
United States
Colleen D.
The price is CA $265
CA $621 total
includes taxes & fees
Aug 4 - Aug 5
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Beautifully appointed, clean and comfortable. This place is worth it! We had a great stay. Location is also excellent. Would definitely stay here again. "
United States
Erica C.
The price is CA $259
CA $613 total
includes taxes & fees
Aug 4 - Aug 5
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

10. 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)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
The price is CA $239
CA $627 total
includes taxes & fees
Sep 2 - Sep 3
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

11. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (39 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is CA $183
CA $553 total
includes taxes & fees
Aug 11 - Aug 12
Charming Home in Key Largo

12. Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is CA $204
CA $582 total
includes taxes & fees
Sep 2 - Sep 3
Flamingo Flats Ocean Pointe 5306 2BR/2BA

13. 4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (48 reviews)
"We were two couples staying in this space with plenty of room. All the amenities on this property (pool, beach restaurant and bar)made this a terrific stay. "
United States
Donna B.
The price is CA $276
CA $635 total
includes taxes & fees
Aug 4 - Aug 5
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

14. Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"Loved the beach and pool."
United States
Haley P.
The price is CA $239
CA $629 total
includes taxes & fees
Aug 24 - Aug 25
Lazy Daze Double King Suite Ocean Pointe 2310

15. 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, (10 reviews)
"Such a beautiful condo! We loved our stay."
United States
Bethany B.
The price is CA $239
CA $627 total
includes taxes & fees
Sep 2 - Sep 3
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

16. 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, (49 reviews)
"This was the perfect little home away from home! The house was perfectly clean and nice and cool! The AC in the bedroom was fantastic and kept the room a perfect temperature for sleeping. In addition the bed was super comfortable! We had a great time in the campground and were so excited about the kayaks available for our use. We have already recommended this house and the campground to our friends and family and can’t wait to come and stay again soon!"
United States
Carrie D.
The price is CA $97
CA $391 total
includes taxes & fees
Aug 25 - Aug 26
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

17. Boho Chic Ocean Pointe 3214 King & Queen

Boho Chic Ocean Pointe 3214 King & Queen
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"The condo was nice and clean. The view from the balcony is very nice. The property is also nice with things to do but not too busy. The host was great and responsive. "
United States
Anthony F.
The price is CA $217
CA $598 total
includes taxes & fees
Sep 2 - Sep 3
Boho Chic Ocean Pointe 3214 King & Queen

18. Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.6 out of 10, Exceptional, (10 reviews)
"We had a great time and the property was the center-point of our stay. Thanks for making it easy!"
United States
Ty L.
The price is CA $210
CA $588 total
includes taxes & fees
Sep 3 - Sep 4
Reel Key Largo Escape Ocean Pointe 5209

19. 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, (160 reviews)
"Perfect place for family to get away. Plenty of room"
United States
Aaron H.
The price is CA $252
CA $644 total
includes taxes & fees
Sep 3 - Sep 4
3212 Across from Pool * King & Queen/Twin Bunk Bed

20. Key Largo Baha Penthouse Ocean Pointe 1416

Key Largo Baha Penthouse Ocean Pointe 1416
Tavernier
9.8 out of 10, Exceptional, (26 reviews)
"Very nice penthouse and enjoyed our visit"
United States
Allen
The price is CA $217
CA $598 total
includes taxes & fees
Sep 2 - Sep 3
Key Largo Baha Penthouse Ocean Pointe 1416
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Upper Matecumbe Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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