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Cottage holiday rentals in Monroe County

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Popular amenities for cottage rentals in Monroe County

Cottage rentals with a hot tub

Superhost

Cottage

4.89 out of 5 average rating, 63 reviews

Turtle Cove Views at Venture Out

ToniRating, 5 stars2 months ago
We absolutely loved this cute little house. It was very clean, very well decorated and in a peaceful little community only 30 minutes outside of key West. We loved the pool and the hot tub. The only negative thing was the house did not have heat and at one point it got down to 66° inside. luckily the host was kind enough to bring us extra blankets. I would happily stay here again, but would pick a warmer month with less wind.
Superhost

Cottage

4.86 out of 5 average rating, 35 reviews

Tidewater Views at Venture Out

AmberRating, 5 stars6 months ago
Would definitely recommend Last Key.
Guest favourite

Cottage

5 out of 5 average rating, 9 reviews

New 150 ft Dock/Private Swim Spa/Tiki/Outdoor Bar

KathyRating, 5 stars1 month ago
As we were arriving Christmas Day and not knowing what would be open for groceries, Sean provided a number of food items and a bottle of wine, which was unexpected, but very much appreciated. Having rented a number of vacation rentals this was the cleanest unit we’ve ever stayed in. The swim spa and the kayaks added to the fun we enjoyed. Sean was very responsive with helpful information before and during our trip. Highly recommend booking Sean’s place now or in the future.

Cottage

4.81 out of 5 average rating, 95 reviews

OCEANIA... water front cottage retreat ~

RachelRating, 5 stars4 months ago
If we could rate this 6+ stars out of 5, we would! Manuel was super easy to reach, he provided simple and clear instructions, the guards at the gate were easy to work with and available for 24/7 entry and check in.. the location is unbeatable for a boat owner! You dock right at your back door, clean your fish at the back door OR at the marina, immediate access to the Atlantic.. perfection. The home itself is extremely clean & beautiful. The kitchen and bathrooms were all stocked with anything you’d need as well as even the laundry room! We truly felt at home but twice as relaxed! Thanks Manuel!!
Superhost

Cottage

4.65 out of 5 average rating, 108 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

DonnaRating, 5 stars3 months ago
in the photographs the pool looked closer to our Airbnb. other than that everything was just perfect. Jason responded right away to any questions I had and made it very easy. I would recommend his place to anyone. thank you so much

Cottage

4.7 out of 5 average rating, 137 reviews

Calypso Cottage

CoriRating, 5 stars1 month ago
Exactly as described and good location. About 30-45 minutes from Key West activities and a lot of stuff to do at the house - we loved the kayaks, bikes, and pool.

Cottage

4.9 out of 5 average rating, 148 reviews

ATLANTIS...Ocean Front Cottage Retreat!

KelliRating, 5 stars1 month ago
This place was a wonderful spot for our family vacation to the Keys! It is a short and easy drive to Key West and we used the kayaks and enjoyed fishing right off the back deck. the view is amazing. We would definitely stay again!

Cottage

4.93 out of 5 average rating, 57 reviews

NAUTILUS...ocean front cottage retreat ~

KristinaRating, 5 stars2 months ago
Our stay was absolutely great, exceeded all expectations. The house was clean, cozy, with gorgeous views, and exactly as described in the listing. The host was incredibly welcoming and responsive, making sure we had everything needed. Will definitely stay again if in the area!

Pet-friendly cottage rentals

Guest favourite

Cottage

4.97 out of 5 average rating, 71 reviews

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

SusanRating, 5 stars1 month ago
The space was perfect for us! We hosted our grandchild for an evening, and being able to separate the spaces within the dwelling was excellent! We had space for baby, puppy, our bedroom, and a general space for kitchen/entertainment area. Betty cleverly provided areas that could be opened or closed according to your wishes. The inside of the Bungalow was so comfortable, well stocked, and laid out perfectly. The outside was paradise… so relaxing on the bench swing under the Tiki hut, and plenty of room for a family to enjoy relaxing by the water. Neighbors were very friendly, and having a baby pool separate from the main pool was fantastic! I could go on… but take home is Betty takes pride in her home, and hopes others do to! Thanks Betty for sharing your abode with us… had a lovely time!
Guest favourite

Cottage

4.94 out of 5 average rating, 62 reviews

Spacious cottage - the Calusa campground-keylargo

AndreaRating, 5 stars1 week ago
We had a wonderful time at JC’s place. It’s on a campground right at the marina with a lovely heated swimming pool, playground, and basketball court. Very well equipped with an outdoor kitchen for grilling cooking and a lovely seating area. The location is perfect close to grocery stores and lots of attractions. There’s a lot of things to do nearby (10-15 min drive) like theater of the sea, the scuba diving museum, snorkeling, and kayaking . JC was very responsive and helped us immediately. Would love to stay there again. highly recommended!
Guest favourite

Cottage

5 out of 5 average rating, 66 reviews

New Modern Near Airport - Cozy Very Clean

AlanRating, 5 stars1 month ago
Amazing host! Amazing little place to get away too!!!! Everything was spotless and Alex was a very friendly and amazing host!!! Super responsive and sweet and helpful!!! Book with them!!!! Nobody else! 😆
Guest favourite

Cottage

4.97 out of 5 average rating, 32 reviews

Waterfront Cottage Walk to World Famous Lorelei

KatherineRating, 5 stars1 month ago
Certainly! Here’s a draft for your review: We had an incredible stay at the Waterfront Cottage in Islamorada, FL! The property was everything we hoped for and more. One of the highlights of our trip was spotting manatees in the morning right in the channel next to the dock—truly a magical experience! The location was perfect for relaxation, with easy access to the water and beautiful views. The accommodations were clean, comfortable, and well-equipped with everything we needed for a memorable getaway. We highly recommend this place to anyone looking for a serene Florida Keys escape. We can’t wait to come back!
Superhost

Cottage

4.75 out of 5 average rating, 12 reviews

Cottage w/ Private Yard, Free Kayaks, Boats, Etc

JesslynRating, 5 stars29 months ago
Overall we enjoyed our time here. It can be hard to find from the road but has a rustic charm to it. Enjoyed kayaking and time in the tiki hut by the water.

Cottage

4.55 out of 5 average rating, 20 reviews

Large, secluded 2-bedroom house with private yard

KiaraRating, 5 stars2 weeks ago
This is our second time staying at Craig's place, it really is very nice. We enjoy how secluded it feels and how easy it is to relax. He is a very pleasant host and communicated well. Thanks again!

Cottage

4.76 out of 5 average rating, 29 reviews

Cute 1B/1B Lofted Cottage

KaitlynRating, 5 stars2 months ago
Had a great time staying here in the Florida Keys. Location is great and can walk down to see the gulf. AirBnB was clean and had great amenities!

Cottage

4.74 out of 5 average rating, 136 reviews

1BR | Dog Friendly | Deck | Grill | AC

GeraldRating, 5 stars1 month ago
The location was fantastic. It is right in the middle of all the action and an easy walk to everything. The front porch was very nice as well as the courtyard area. As described in other reviews, it could use a little bit of TLC but that did not affect our stay. The bed was super comfortable and the two full bathrooms were a plus. I would recommend.

Private cottage rentals

Guest favourite

Cottage

4.96 out of 5 average rating, 70 reviews

Islamorada bungalow 2 beds & pool

LeslieRating, 5 stars4 days ago
This little bungalow was picture-perfect, meticulously maintained, and gorgeously decorated. We felt right at home - comfy bed and comfy furnishings both inside and out in the front porch. We used the fire pit and the bikes, but there was so much more available to us (paddleboards, cornhole, etc) so it was lovely having so many options. The pristine pool was only steps away and was never even close to crowded. Yasmin & Joe were so thoughtful and responsive. I highly recommend their place to anyone looking for a lovely getaway in Islamorada!
Guest favourite

Cottage

4.98 out of 5 average rating, 84 reviews

Oceanfront Paradise w/ Amazing View! Kayaks & BBQ

LilienRating, 5 stars1 week ago
The place is amazing. Clean, bright, quiet. But the view!!! The view is all. It is a very relaxing place, amazing to just seat outside and enjoy the peace. One observation only, I recommend going in one car. There are not many parking spaces if you are traveling in more than one vehicle. Everything else is 5 stars.
Guest favourite

Cottage

4.96 out of 5 average rating, 28 reviews

Catch n' Relax Canalfront Cottage in Marathon

JodiRating, 5 stars1 month ago
Highly recommend for a stay in Marathon. We did not have a boat but it is a great location for yours. Quiet neighborhood. The owners have put a lot of effort into making your stay comfortable.
Guest favourite

Cottage

4.96 out of 5 average rating, 26 reviews

Waterfront cottage w/ MotherInLaw suite&boat slip

RachelRating, 5 stars6 months ago
We absolutely loved this charming cottage and Conch Key. Barry made sure we had everything we needed, and offered advice and insight into the surrounding area. The views from the dock and the character of the cottage made our trip everything we wanted it to be. We will definitely be back!

Cottage

4.72 out of 5 average rating, 359 reviews

1 bedroom Cottage

JoseRating, 5 stars1 month ago
I will return. Would recommend to anyone who wants a good time or quiet time or relaxing time
Guest favourite

Cottage

4.91 out of 5 average rating, 67 reviews

THE PARADISE

ChristinaRating, 5 stars3 weeks ago
It was a beautiful location. We fished off the little dock for fun and caught some fish! The house was beautiful and very clean! Even had some fishing poles and a kayak we could use. The neighbors to the left were so AWESOME! We WILL be staying here again!!! Thank you so much for allowing us into your home!

Cottage

4.77 out of 5 average rating, 75 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

DoJoRating, 5 stars2 months ago
we had a great stay at Carol's property. It was top notch and we'll worth it. Carol was also proactive and helpful with everything. We highly recommend Key Lime Cottages. The area is Very safe and fantastic with restaurants and all the services you can think of. Thank you Carol and Team for an amazing experience. 🙂🙏❤️
Superhost

Cottage

4.83 out of 5 average rating, 40 reviews

Welcome to the Islands- Pool-Marina-Kayak

YunietRating, 5 stars5 months ago
Very good stay. The only two things I’d have to note is, first, regarding the bedroom on the back. It doesn’t get too much ac and can be on the hotter side even tho It has its own ac unit, it will only start from time to time and it’s quite loud so it might wake you up a couple times at night. Also, the sofa was not very comfortable to sleep in, I think it needs te be taken care of a little bit. Other than that the place was really clean and the host is very responsive and proactive, no complaints there.

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