Apartment holiday rentals in Big Pine Key

Ocean Isles is a beautiful property. Very quiet and calm. Everyone we encountered was so friendly. Great views! Nice amenities and property had box of fun extras…we had to leave a couple behind to add to the stash. Great communication. We definitely will be booking again in the future.

A wonderful place for our family to enjoy Key West! The unit was exactly as described and very easy to access. Host was communicative leading up to and throughout our stay. Excellent value, and I would highly recommend!

Beautiful little apartment right on Duval Street. Really was a small slice of paradise.

This is our second time staying at this location and it honestly couldn’t be any better. The people around the marina are very friendly and inviting and the host is very responsive. We look to return soon.

The apartment was easy to book, easy to find and easy to access. It is in the middle of the island (east-to-west), just off Duval St. (the main drag), so it is very convenient. I rented a bicycle for transportation during my stay, and the fenced, gated, secure patio was the perfect parking spot when I was "home." The interior was clean, comfortable and beachy. It had everything I needed with the expected luxury-accommodation quality. Do note that there is no dishwasher or clothes washer/drier, but I knew this ahead of time, so it was no problem. The management office is just around the corner, and they have a nice service where you can drop off your luggage for day-storage if you arrive prior to check-in time.

Absolutely awesome spot. The dock is a little reef itself and is covered in parrotfish, grouper, and snapper. Easy docking! Couldn’t have asked for anything more.

My boyfriend & I have been coming to Skipjack for his birthday for the last two years & we absolutely love it ! It has become a little tradition. We love the space and the dock in the back! During our stay we saw a manatee, a Manta Ray, & lots of Tarpon in that canal. Absolutely beautiful. The location couldn’t be better as it’s right in marathon, where you are close to Sombrero Beach, Publix, lots of delicious restaurants with great ambience, etc! We look forward to our next stay at SkipJack!! :)

Our unforgettable stay at this oceanside Airbnb resort on Big Pine Key was nothing short of extraordinary!! Even before the moment we arrived, the staff’s warmth and dedication made us feel like family. Every detail, from the included bicycles and complimentary kayaks to the Key Deer roaming freely near the resort’s lush grounds made it so captivating. With breathtaking—pristine beaches, stunning ocean views, and beautifully designed accommodations that blend luxury with coastal charm. The Staff truly went above and beyond to accommodate our needs. Due to unforeseen errors prior to arriving, I had some hurtles to overcome which they did and amazing job assisting with. Their attentiveness and genuine care elevated our experience to another level. The resort’s amenities, including the magnificent facilities with stunning architecture and private beach access were impeccable, and the serene atmosphere made it impossible to leave. Five stars aren't enough for this slice of paradise!

We had a fantastic stay at Tranquility Guest House — we were able to check in early and everything was already clean and prepared for us. The host was very responsive and helpful with messaging which was reassuring. The pool is also clean, quiet, and private. Overall this is a great value for the money and the location is perfect!

Great place to stay for nightlife and shopping and very central location. Big room with lots of space and seating. Enjoyed that the bike and scooter rental were right down the street and Cuban coffee queen right down the stairs for a great coffee every am! Pleased with this unit and would definitely stay here again- do bring your own shampoo and conditioner and coffee just fyi. There was a small shampoo but no conditioner! Overall incredible place to stay! And the Host was so responsive and answered questions really fast!

Magen was very easy to work with. The place was very clean. Would definitely stay there again. Thanks Magen!!!

Thomas has excellent communication skills. Quick responses to enquires. Great location right on Duval st easy walks to both ends of Duval St. this was my second stay there both turned out great.

Great spot, Everett was easy to get ahold of and we were able to check in early by messaging them.

This is a nice place with parking included and a nice swimming pool. It is right at Duvall street and 20 minutes walk with toddler to the Mallory square and 15 mins walk to the Southern most point. Sunscreen and aloes and beach towel and a candy jar is provided at the general area which is a nice touch. There are 2 roosters and hens and baby chicks hanging around at the parking lot area is pretty cool . Overall is very nice and will go back for sure

This place and its host were awesome. Such a great location, a great space, and wonderful host with clear instructions and great communication. We would definitely highly recommend!!!

Naomi was an amazing host, and always there if you need her! We had an unexpected situation arise during our trip and she had our back and was so helpful and accommodating. She is a genuinely kind person and this place is in the perfect location. Would love to stay with her again, and thank you for being so welcoming to our furry family members!

Nice cozy spot while visiting Key West.

We previously stayed on this property in the upstairs apt and liked the convenience to everything. Across the street is Ramshead Live. Down the block is Blue Heaven and other amazing restaurants. This space is secluded and we loved the hot tub. The bed was also very comfortable.

We loved our stay with Teri and Scott! Nice location convenient to the airport. Beautifully renovated. Was just what I needed for a group of 4-6. Thanks again yall!

Perfect location (see sunsets from property, right next to docks where many ocean excursions can be booked) and great amenities (great pool with palm trees and hot tub with ocean views). There is also an on-site concierge to help you book anything from scooter rentals to activities/excursions. Samantha was incredibly accommodating. 10/10 would book again.

Place was great, used pool and hot tub every day of our stay was private bc no one else did, house had plenty of kitchenwear, walkable to duval st and Mallory square didn’t have to drive anywhere, upstairs neighbors were a little noisy but that’s no fault of the owner, had a great stay would return

Beautiful place with a well stocked unit…close enough to all the places we wanted to visit, yet far enough away for a quiet, relaxing day. We loved the area and our stay here. Thank you, Chris.

Had a great stay, very clean and nice community

The Condo was spacious, beautiful, well furnished, very clean and the location was perfect. Henry was great to work with. We rented a golf cart and traveled almost everywhere in Key West by golf cart.