Vacation rentals in Upper Matecumbe Key

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Top-rated vacation rentals in Upper Matecumbe Key

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Guest favorite

Apartment in Tavernier

4.89 out of 5 average rating, 434 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

Capt. Craig’s Guest Quarters The Starfish is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From watersports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled with the traveler in mind, enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer.

Jun 5 – 12

ﺩ.ﺇ705 per night

Guest favorite

Home in Islamorada

4.94 out of 5 average rating, 17 reviews

3 Lux Ensuites Walk/Boat Island!

Dive into the heart of Islamorada and COUPLES Imagine: THREE MASTER BEDROOMS, so no squabbles over only 1 Master! This 2017 townhome promises restful nights and lively marine filled mornings. From your balcony, salute serenity; Dockside bid sunsets a farewell or mingle with manatees and lobsters. A stroll away: world-class dining, boutiques, bars or a Paddleboard escapade. Welcome to bayside luxury with a splash of fun! Explore the community & nearby libations. Your tranquil Bayside haven awaits

Feb 22 – Mar 1

ﺩ.ﺇ2,096 per night

Guest favorite

Cottage in Islamorada

4.95 out of 5 average rating, 40 reviews

Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

Sep 22 – 29

ﺩ.ﺇ1,583 per night

Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Aug 2 – 9

ﺩ.ﺇ798 per night

Guest favorite

Condo in Tavernier

4.95 out of 5 average rating, 106 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

Jul 28 – Aug 4

ﺩ.ﺇ887 per night

Guest favorite

Cottage in Islamorada

4.94 out of 5 average rating, 16 reviews

Waterfront Cottage Walk to World Famous Lorelei

Waterfront Conch Cottage. Short walk to world famous Lorelei for sunset celebrations. Custom length of stays can be arranged if booking a sandbar/sunset/fishing charter with our family business. The cottage was built in 1940s and still has the original hardwood floors, open beam ceilings. Private yet in the heart of Islamorada. Walk to two local craft breweries nearby! This listing is new to AIRBNB but booked for many reservations thru VRBO all 5 star. One pet only under 20lbs. /pet fee $150

Apr 17 – 24

ﺩ.ﺇ1,206 per night

Guest favorite

Home in Key Largo

4.98 out of 5 average rating, 118 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Sep 17 – 24

ﺩ.ﺇ784 per night

Guest favorite

Boat in Islamorada

4.9 out of 5 average rating, 169 reviews

HOUSEBOAT 2BD, PRIVATE KEYS COTTAGE LOGGERHEAD

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Sep 1 – 8

ﺩ.ﺇ638 per night

Guest favorite

Home in Islamorada

4.97 out of 5 average rating, 165 reviews

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Nov 30 – Dec 7

ﺩ.ﺇ967 per night

Guest favorite

Boat in Islamorada

4.92 out of 5 average rating, 327 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Jan 28 – Feb 4

ﺩ.ﺇ686 per night

Guest favorite

Home in Islamorada

5.0 out of 5 average rating, 10 reviews

Heart of Islamorada ~ Private Boat Slip

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle to every place in town. Truly in the heart of Islamorada, yet secluded within a protected cove among the mangroves. Our development is located directly on the bay, with easy access to boat dockage, a community pool, and water sports. Less than a mile away from many of the best restaurants, bars and shops in town.

Sep 24 – Oct 1

ﺩ.ﺇ3,436 per night

Guest favorite

Guesthouse in Key Largo

4.91 out of 5 average rating, 190 reviews

Oceanside, 1 bedroom, Bungalow in Key Largo

Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.

Aug 19 – 26

ﺩ.ﺇ743 per night