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.

Great location. It felt very quiet and peaceful. We didn't have the best weather so we didn't get to enjoy all the amenities of the property but it felt walkable.

such a quiet place to have our honeymoon. so cute and the people are so nice. nice area to get away and to explore on your free time. overall just an amazing experience. would do it again and again ❣️

This was a repeat stay with us at Darene's place, and we will come again. Darene is great with communication and responds quickly. Her place is great! The ocean view never gets old. The beach at the condos is perfect, and the proximity to the pool is also perfect! The condo is nice and accomodating. The beds are very comfortable. We had everything that we needed during our stay, and we can't wait to return again! Thank you Darene!

A great place to stay for a couple days in Key West. Everything was very clean and in good condition. We really enjoyed being able to sit on the balcony overlooking Duval for a little downtime. Highly recommend.

Wonderful place for a couple to enjoy walking and bike riding to everything. Perfect spot. Host was very responsive. Definitely would stay here again.

Wonderful views, quiet. Clean and had free laundry. Just what we were looking for. Beautiful property with balcony, patio and rooftop deck. Centrally located and close to shopping Good places to eat nearby

LOCATION! Highly recommended. We rented Jack’s place for my husband’s 40th birthday trip. Walkable to all the restaurants, bars, activities, yet perfectly tucked away. Loved how there were two locked gates making this space feel nice and private and safe when we weren’t out and about. We shared the space with a friend couple and it was perfect. Great kitchen - all you need.

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

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

We really enjoyed our stay in Key West. This apartment is in the best location. We will definitely be back . If you’re looking for a place to stay and want to be able to walk and enjoy Duval Street definitely stay here. We also loved the little balcony for people watching and relaxing.😁 There’s golf cart and bike rentals across the street . Great location !

I’ll be back ASAP. Great location. Great staff. Felt private. The pools and jacuzzi and marina especially were valued

Beautifully decorated, perfect size for a couple. Great location for days trips to the different keys. Lovely lady next door. Coin operated washer/dryer just steps from the condo. The condo does require additional paperwork and a deposit may be required during the booking process. Recommend the kayak eco tour in Tavernier and Theater of the Seas.

The tranquility guest house was such a great place to stay! In a great location with 3 very delicious food options within 1-3 min walk! Also a very short walk to get to Duval street! I highly recommend this location to stay!

I loved it so much I booked another stay in October. Great location. Great staff. Quiet and peaceful. Walking distance to great restaurants. enough kitchen space to eat in. I was very happy with my stay.

Very nice condo beds were comfortable. Nice view on the 4th floor. Would definitely book again here.

Nice cozy spot while visiting Key West.

When I say that this is the most perfect Airbnb I’ve ever stayed in, I am not joking. Tina’s place is a gem in the upper Keys. Super close to John Pennekamp State park, good restaurants, and even better bars. I was able to show family who had never been to the Keys just how beautiful it truly is. Tina’s place drove that point home! I can’t wait until I have the chance to stay here again!

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!

lots to do. beautiful pool

We had a great time at this home during Memorial Day 2025 in Key West. Good amenities and walking distance to all of Key West downtown bars,shops and restaurants.

Had a great stay, very clean and nice community

This is a beautiful condo in a great community. My 3 teens loved hanging out at the pool and the beach area. The bar on premises was an added perk and had a great menu.

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.