Tiny house holiday rentals in Monroe County

Great place to stay. Really peaceful. Thank you!

We absolutely loved this cute, cozy little space. Sergio was amazing responding so quickly to requests. Parking was easy, check in was easier, the space was quiet after dark, and I LOVED all the wildlife. Stay here. You won't regret it!!

We stayed at this wonderful houseboat as we began our trip to the Florida Keys and it was perfect! We saw manatees, enjoyed dinner at the outdoor bar with locals, and had a beautiful view of the sunset. Great location with a wonderful host!

Great tiny home right on the water. The best view in the park! Great tiki hut outside with picnic table which we used everyday! Cute lights outside. Appreciated the second half bathroom. Kitchen and living space was good and house is close to laundry and right across from pool. Loved our vacation! 5 stars!!

This is the perfect location for us, we have a small flats boat and there’s great fishing in the area. The weather was not great but were able to find areas to fish sheltered from the wind. When not fishing, hanging out on the dock with Princess, watching the manatees and having a cold drink was absolute paradise. Penny is very responsive and was available anytime needed. This was our second time staying at this location and already talking about booking a longer stay next year.

Phenomenal. A little oasis. Veronica is extremely helpful and communicative. The place was clean and thoughtfully curated - probably the homiest place I've lived in. Enjoyed my 6 weeks here immeasurably. The outside area and quiet neighborhood, easily accessible to other areas were the highlights. Vero & Eric are very friendly and I always felt comfortable with them. Thanks for a wonderful stay!

Cute and very cozy place in a beautiful neighborhood. Unit looks as pictured. James was an excellent host! Very responsive. I truly appreciate his kindness with accommodating earlier check-in and later check-out times which was great for my flight schedule. I was very pleased and would definitely stay here again ☺️

Excellent place to get away for a weekend

Wonderful place to stay at. I recommend staying here. My husband and I were able to fish right off the dock, even rented a boat from the marina. This place is paradise.

Super cool place to stay. Clean and the outside is beautiful. So peaceful ☺️ Frank is really nice , answers quickly! We definitely will recommend to friends and family.

Great use of space! Extremely clean! The little yard surrounded by plants provided privacy. I would definitely stay here again and would recommend to anyone staying in the Big Pine Key area.

Wonderful host!! Very responsive! Cute tiny house great for a few days stay! Great restaurants within walking distance!! Highly recommended!

Carla was amazing! She was super responsive and so accommodating. We had an issue and she got it dealt with quickly. Place was in a great location and was super homey with a lovely hot tub. We caught fish and we cooked it right there. Definitely will stay again!

We had such a good time! The back yard atmosphere was so epic. We grilled steak. We played pool. We relaxed in the hot tub. My fiancé slept in the hammock. We watched movies outside on the couch under the patio lights and stars. We rode bikes to Pigeon Key. The 7 mile bridge is epic. Tour guide Eric knows his stuff You really feel attached to the community rather than a tourist here. The Cracked Conch across the street was rad. There’s a bike rental place a mile away. A Publix across the street. And if you want to save money on eating out the stove comes in handy. My fiancé made fresh boiled stone crab from Key Fisheries, an awesome non pretentious bar/fish market down the street. And then some fresh swordfish from Publix 1 hr from key west. We bar hopped on Duval St. GOT ENGAGED. We would’ve went parasailing but we literally missed the boat lol Awesome awesome time. Lots to do

Good location on Big Pine Key and would serve as a convenient base if you want to visit multiple keys. The neighborhood seemed safe.

From the time we arrived Ivan was attentive. He made me feel right at home. His attention to detail was impeccable. He gave me suggestions of places to eat, and they were spot on. Ivan is very detailed and thorough. Everything you need is there. Very clean. Honestly, I can't say enough good things about our stay there. The only thing I will warn you of is the mosquitos in the Key Largo area. Please bring some repellent because you are going to need it in June. I definitely recommend Ivan's Tiny house. If you never had a sort of camping or outdoor experience, try this area. There are RVs and Tiny Houses. There are some three-story buildings too. The guards are very nice at the gated entrance. Check in was a breeze. Pay 10.00 for registration, show your ID, get a map of the area and you are done. My grandkids played basketball at the full court, and they went fishing. The younger ones played at the playground. They also have a food truck by the pier. You won't want to leave Ivan house .

A quaint and novel place to stay in the historic Cocoanut Grove Park neighborhood. Perfect for 1-2 adults and 1 small child. Beautiful neighborhood to walk or run with mature Banyan trees and peacocks. Plus a 1/2 mile walk to downtown Cocoanut Grove. The Water Tower is located on beautiful property with wonderful outside common space for sipping coffee in the AM or wine in the evening. WiFi and set up of NetFlix on the TV was available and easy to access. Carole, the host, is friendly greeting me and family members as we were enjoying the outside space as a respite following my son's UM Grad Ceremony. I definitely plan on reserving the Historic Water Tower for my next visit to Miami!

Betty is a wonderful host! She makes sure her guests feel at home. We've stay at her place multiple years and we always have a fantastic experience! It's a great place to do some relaxing, boating and fishing!

Had a wonderful time here, it’s close to everything, and a nice running path where I could take my dog every day. The host Terri was very responsive. Will definitely come back.

We absolutely loved it here! The place was clean, easy to find, and beautiful! It looked exactly like the photos and plenty of amenities which made our stay feel like we were right at home. We were even able to bring our paddle boards and swim in the canal outback which only made our stay even better. I can’t wait to book this home again for future vacations!

Place was great! Everything was clean and community pool was a great close option for enjoying some time outside. The bikes were super helpful for a quick run to the grocery store just a few minutes away. There is a small beach just down the street from the unit, though it was mainly just an access point to a channel filled with mangroves, so we didn’t spend much time there. Be mindful when booking that you cannot check in after 11pm. This is part of a gated community, and entry will not be possible after hours without the key card that you get from the front office at check in. Once you have the key card though, you are all set to come and go as you please. That being said - I highly recommend this unit to anyone who will be arriving before the 11pm cutoff time!

Jhonnathan is a fantastic host, he made sure my family felt right at home. Location was better than expected with many things to do near the house. I will definitely keep this place in mind for future travels.

We stayed in two smaller house boats while we were there before brads. Rectangular shaped single stories with a flat roof area for lounging. They were beautiful.. but unstable, uncomfortable, limited in space, no hot water, had to shower 200 yards away, awful mosquitos, no reliable internet, lack of kitchen ability, I’m 32 my wife is 30 and our son was five months. Pretty looking, but miserable. Especially if wind wasn’t below 5mph. Not to mention the toilets had problems on both! When we got to brads house boat Holly Cow! What a difference. What a relief. Multiple rooms, comfortable beds, no issues with hot water or internet or kitchen. The space was excessive. Very comfortable. Needed some TLC inside but overall it was fantastic. Everything worked like a real 2br 3ba home. I will book this boat everytime as long as it lives. Private marina, quiet, great neighboring boats. Private outdoor waterfront recreational areas. 100% best key west experience I’ve had and I go every year.

Liza is a wonderful host! We had an issue with our initial week of reservation and she graciously worked with us to move the dates. Her home is very clean, relaxing, and centrally located within the campground...just a few minutes walk to pool, playground, and laundry facilities. Thank you for sharing your home with us!