Vacation rentals in Craig Key

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Top-rated vacation rentals in Craig Key

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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

R8,261 ZAR 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.

Jul 4 – 11

R4,163 ZAR per night

Guest favorite

Home in Islamorada

4.96 out of 5 average rating, 55 reviews

Tropical Getaway 3/3 with 100’ boat dock and pool

Located in Lower Matecumbe Key, a part of Islamorada, this piece of paradise checks all the boxes all the way down to a putting green! World class everything awaits you after an idle down the canal with quick access to the Atlantic Ocean. Bayside accessible via one of the nearby bridges. 100’ dockage with a covered fish cleaning station is available for your fresh catch of the day. Whether you’re here to fish, sunbathe, snorkel, or enjoy some fantastic seafood, this is the place for you!

Nov 18 – 25

R9,959 ZAR per night

Superhost

Cottage in Islamorada

4.81 out of 5 average rating, 142 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

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. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

Sep 12 – 19

R3,331 ZAR per night

Guest favorite

Home in Islamorada

4.97 out of 5 average rating, 164 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.

Dec 7 – 14

R5,045 ZAR per night

Guest favorite

Boat in Islamorada

4.92 out of 5 average rating, 325 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 8 – 15

R3,582 ZAR per night

Guest favorite

Apartment in Key Largo

4.92 out of 5 average rating, 228 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Enjoy gorgeous sunsets and excellent views of Manatee Bay from this beautifully upgraded studio apartment. The perfect spot for couples and small families, this modern studio comes with kayaks and paddle boards so you can get out on the water like a local. The ideal location offers easy access to the Bay, great restaurants, and local beaches. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park Experience Key Largo With Us & Learn More Below!

Aug 22 – 29

R3,466 ZAR per night

Guest favorite

Home in Marathon

4.96 out of 5 average rating, 123 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Jul 22 – 29

R10,066 ZAR per night

Guest favorite

Cottage in Islamorada

4.97 out of 5 average rating, 65 reviews

Key Lime Cottage 2br 1ba w/pool

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

Oct 27 – Nov 3

R7,015 ZAR per night

Guest favorite

Bungalow in Islamorada

4.97 out of 5 average rating, 29 reviews

Dream in Paradise! King Master, Queen Guest, Pool

Castaway Island! Luxury In paradise! This hidden gem is your piece of paradise waiting! Fully remodeled and furnished from the floor up. All new furniture, fixtures and furnishings await. One of the most well appointed and private Bungalows in Islamorada. Perfect for the honeymooners and special occasion couples and small families. Private outside spaces. 4 Bikes, 2 ultra lite SUP's, 2 Kayaks, 4+ beach chairs, ice chests and more await you.

Feb 4 – 11

R15,234 ZAR per night

Guest favorite

Guesthouse in Key Largo

4.91 out of 5 average rating, 187 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.

Sep 23 – 30

R3,880 ZAR per night

Guest favorite

Home in Key Largo

4.9 out of 5 average rating, 347 reviews

Your Keys Getaway!

Beautiful two bedrooms, 1 bath Keys Home fully renovated interior in a quiet residential neighborhood. Large breeze veranda for open air meals and relaxation. Large fence yard for sunbathing or playing around. Close to restaurants, shopping center, major hospital, beaches, parks and water sport activities. Perfectly located between Key Largo and Islamorada. Once you've been here you will want to come back.

Jan 18 – 25

R3,560 ZAR per night