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Vacation rentals in Monroe County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Monroe County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Cottage in Islamorada
1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
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.
Aug 20 – 27
$169 per night
4.85 out of 5 average rating, 121 reviews
Superhost
Villa in Marathon
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!
Jul 9 – 16
$288 per night
4.88 out of 5 average rating, 128 reviews
Guest favorite
Home in Marathon
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!!
May 13 – 20
$400 per night
4.96 out of 5 average rating, 114 reviews

Popular amenities for Monroe County vacation rentals

Other great vacation rentals in Monroe County

Guest favorite
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
Nov 30 – Dec 7
$422 per night
4.91 out of 5 average rating, 142 reviews
Superhost
Condo in Key West
Beach Club Ocean Front 2BR Condo
Jul 23 – 30
$613 per night
4.93 out of 5 average rating, 132 reviews
Guest favorite
Farm stay in Homestead
Charming Farm Studio, Near Everglades & Keys
Aug 23 – 30
$92 per night
4.96 out of 5 average rating, 147 reviews
Guest favorite
Tiny home in Key Largo
The Oasis in key largo with your own private beach
Jun 30 – Jul 7
$244 per night
4.97 out of 5 average rating, 158 reviews
Guest favorite
Guest suite in Homestead
Cozy 1BR guestroom, private entrance, free parking
Dec 21 – 28
$74 per night
4.92 out of 5 average rating, 112 reviews
Superhost
Houseboat in Key West
Happys Houseboat
Jun 4 – 11
$387 per night
4.85 out of 5 average rating, 163 reviews
Guest favorite
Guest suite in Marathon
Casa Mariposa: Easy walk to Sombrero Beach
May 16 – 23
$189 per night
4.98 out of 5 average rating, 177 reviews
Guest favorite
Tiny home in Cutler Bay
Quiet tropical Oasis setting with 1 bed and 1 bath
Apr 29 – May 6
$126 per night
4.99 out of 5 average rating, 138 reviews
Guest favorite
Apartment in Key West
Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
Jan 22 – 29
$295 per night
4.97 out of 5 average rating, 438 reviews
Guest favorite
Condo in Key Colony Beach
Oceanfront Breeze, Stunning Views, Beach/Pool
Oct 30 – Nov 6
$298 per night
4.92 out of 5 average rating, 189 reviews
Guest favorite
Home in Cudjoe Key
Paradise and Cudjoe Bay
Dec 9 – 16
$359 per night
4.94 out of 5 average rating, 131 reviews
Superhost
Houseboat in Key West
The Crystalmarine Suite – Rustic Luxury on the Sea
Sep 30 – Oct 7
$455 per night
4.96 out of 5 average rating, 26 reviews

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