
Monthly Rentals in Craig Key
Discover long-term rentals that feel like home for stays of a month or longer.
Nearby monthly rentals
Superhost

Apartment in Islamorada
5 out of 5 average rating, 3 reviewsOcean View Duplex Penthouse | Pool | Vista Two
AnneRating, 5 stars2 months ago
Beautiful, very clean property with a fantastic location. Excellent proximity to snorkeling, restaurants and other local attractions. Short stroll to excellent walking path that takes you along route 1 with amazing morning views of the beautiful water. Great views all around, in fact. Plenty of soft, plush towels and similarly luxurious bed linens. We had a wonderful family vacation staying at this property.
Guest favorite

Condo in Islamorada
5 out of 5 average rating, 7 reviewsIslamorada Ray
MattRating, 5 stars3 months ago
We thoroughly enjoyed our stay at this property. It was exactly as described in the listing. The location is in a vibrant, trendy area, surrounded by art galleries and excellent shopping options. The rental itself is high-end, featuring upgraded furnishings and tasteful décor throughout. The outdoor area is both comfortable and well-maintained, providing a perfect space to relax. There are numerous restaurants in the vicinity, and just a short walk across the street offers beautiful sunset views. We were so impressed with our experience that we are already planning to return next year. Thanks, Matt
Guest favorite

Home in Islamorada
4.88 out of 5 average rating, 8 reviewsPrivate Keys Home with Boat Ramp + Beach!
JonRating, 5 stars9 months ago
Fantastic spot to take a boat or just fish from the dock and hangout. Very nice clean home. We are a family of 6 so the size was perfect. The canal to bay access was great for us as we brought our boat. I launched a 22' center console xpress from the ramp on site and you cant beat the convenience. I don't think you could go much larger of a boat on that ramp but the dock space could certainly handle more if you put in off sight. I would definitely return. Bring what you need as the only thing real close is a corner gas station (walking distance), although publix and good tackle/bait shops aren't really that far up the road.
Superhost

Townhouse in Islamorada
5 out of 5 average rating, 21 reviewsOcean Islamorada BeachHouse POOL!70' DOCK boatrent
OksanaRating, 5 stars10 months ago
Three things come to mind for this property: Clean, Great Location, Outstanding Amenities. Walter and Karen by far exceeded our expectation not only with the property which is great (bikes, pool, dock, ice machine, fish cleaning station, hoses, fire pit) but, are wonder people with lots of knowledge. The location is outstanding for a boater, beachgoer, vacationer wanting a quite place to relax upstairs on the Lanai or take a dip in the pool. Our favorite, was the beach access which we took the bikes to to watch the evening sunset and relax on the hammock while the kids played in the crystal clear water. Being in Islamorada, we enjoyed the local restaurants that are minutes from the property. Pro Tip: There is a fish and lobster market right before your turn into Gulfview Dr. Look for the lobster pots and inside they have fresh fish, lobster and crabs that are freshly caught daily! Big Thanks to Walter and Karen who are outstanding people and great hosts. See you next year!
The comforts of home and great monthly rates
Amenities and perks for longer stays
Furnished rentals
Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.
Flexibility you need
Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*
Simple monthly prices
Special rates for long-term vacation rentals and a single monthly payment without additional charges.*
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Work-friendly spaces for digital nomads
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*Some exclusions may apply in certain geographies and for some properties.