Apartment holiday rentals in Key West

We had a great time! Awesome community with walkable restaurants and bars. We loved the local beaches. The people at the complex were super nice. Our four boys loved running from the pool to the beach. Everyone we met was very nice. Great instructions and recommendations. Loved it!

The condo was well equipped and in a quiet spot. We loved the beach and didn’t have problems finding chairs. It’s not a huge beach so it wasn’t noisy or crowded. The pool is also very nice! There are beach towels, rafts and sand toys in the unit which was great. There is an area under the building with ping pong, a mini pool table and other games too. We have older kids but would’ve loved to have found this place when they were little. It’s perfect for young families with the pool and small beach. We definitely had a chance to unwind during our stay. Desy was super responsive to my questions and messages.

The place was very wonderful and peaceful, perfect for enjoying a relaxing time with beautiful ocean views and relaxing breeze. Plenty of open space right by the water to relax. Apartment was super comfortable with all amenities needed and very clean.

Even better then the pictures. Chelsea was so helpful as a Hurricane was coming in on our trip and she offered to let us come early or stay longer. Fast communication and clear instructions in the welcome and farewell email. We would absolutely stay again. We had a wonderful time and the place was perfect! Highly recommend!

Comfortable, spacious space with all we needed to feel right at home. We loved the neighborhood! Peaceful, beautiful and quiet, yet so close to any restaurant, shop, museum or beach we wanted to go to. We ditched the rental car and walked or rode bikes to get around. The rental is beautiful with floor to ceiling windows to let afternoon sunshine in as well as the garden views from the front porch. The artwork and decor brought in the island vibe … very cozy and carefree. And the Historic Key West Vacation Rental staff were great to work with … responsive and professional. This vacation rental checked all the boxes for us!!

Wonderful resort. Staff super friendly. Loved the pool, and location. Would absolutely recommend!

Great spot to spend days for vacation. Great service by office staff. They took care of all requests we had in the most friendly manner. The hotel is located right on the water, so views were great. Nice pool and great vibe. Would highly recommend.

What a great find I almost want to say nothing and keep this wonderful place to myself but like all great things the word gets out I hope to come back and do it all over again next year a true wonderful find

PERFECT location! The small problem we had with the ac unit was addressed right away with great communication! Would definitely stay there again.

What a great spot! We were blown away by the value. Clean, comfortable and close to literally everything we wanted to do in Key West. They even picked us up at the airport even though our flight was 30 minutes late. Amazing place in an amazing town. We will definitely stay with Rick again!

Great space with everything you need. Patio is a perfect place to relax. The house is well stocked. Plenty of room for a group. Access to hotel pools/restaurant with transportation into town if you need it. Great host communication. All you could want!

Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.

Nice area near the airport away from Duval but easy to get to everything. Kids liked the pool (water was warm and hot tub was hot), comfortable beds and good sized kitchen.

I really enjoyed this place. We have been to Key West many times over the years and this one was in the top 3. Peaceful and quiet. Lovely surroundings within the villas . And yet it was close to everything. Very walkable which in Key West is important. The villa we stayed in was comfortable and clean. We rented mopeds from the business next door and they provided free shuttle back to the airport👍

This condo was everything it said it was. Very clean. Great location, clean and serviceable furnishings and an awesome view. One thing that really struck out for me was that the kitchen had everything that you would need without being stuffed with a lot of extra stuff you don’t need. Also the pots and pans were very clean and almost new. Michael was very responsive to all our questions and made sure that we were happy with everything. We would definitely stay here again and recommend it to anyone interested in staying in Key Largo.

Everything was great! Nice area, and easy access to local activities. we enjoyed our stay.

Great view, easy check in, comfortable stay

We loved our stay at the Dapper Dolphin! The space was so clean. Kate has everything there for you - from beach chairs to laundry detergent! This apartment is conveniently located to great restaurants, attractions and Sombrero Beach. You are just a short walk to the pool at Skipjack Resort. They have poolside karaoke on Monday nights which was very fun. Highly recommend booking this place - we miss it already!

We could not have been more grateful for the stay at Cynthia’s. The setting is perfect - quiet, secluded, right on the water, but a 5-10 minute drive to anything you would want or need (attractions of Key West, Publix groceries, CVs). We did day trips to Key West, Marathon, Bahia Honda, and more. The place is just lovely. The two bedrooms are perfect for a family of four. Our children were very happy and cozy in the room with two single beds. The master looks right onto the ocean. The place is outfitted with everything you need (kitchen needs, etc). The bathrooms are new and nicely redone. The pool is pristine and we often had it to ourselves, but on the occasions we got to say hi to the neighbors they were warm and lovely. One thing that made it extra special was Big Coppit is close to Naval Air Station Key West, so (only during appropriate hours, like 8-9am), we got to see amazing fighter jets fly over head. Cynthia is a great host and was responsive and understanding. Thank you!

Bonnie's place was just what we had hoped it would be. Comfy, plenty of room for 2 friends and not tripping over each other. Ice maker in fridge was a great plus. We loved it and if we're ever in Key West again, we'll ask for this location.

PERFECTION!!! I have so many great things to say about our stay. First, the condo was beautiful and fully stocked. It even had plenty of soap, toiletries, paper products etc to get you started. Yuni was the perfect host and answered all questions and gave clear instructions. The balcony was huge. It was enough for the family to eat and lounge all while enjoying the beach and pool views! Key Colony Beach is a charming community we walked to the sunset multiple nights. My kids aged 10,8,7 did not want to leave. The complex had very friendly retirees and a handful of families with kids. Everyone was super respectful and friendly. The pool was super clean and warm. The beach was groomed each night and the kid had plenty of room to play on the sand and hunt for shells and hermit crabs. Marathon is a great Key to stay on - close to lots of fun activities. We are already planning our next trip and we will definitely rent this condo again! It’s perfect for families!

Kim's place was perfect for our extended family. The full unit (kitchen, lounge, bathroom, and bedroom) downstairs was perfect for my parents to stay while my family of 4 plus my sister stayed upstairs where there is another kitchen and lounge as well as 2 bedrooms. Facilities in the complex were fantastic with a huge pool, tennis and pickle ball courts, and clubhouse. The location was great to get anywhere in Key Largo as well as the rest of the Keys. Last, but definitely not least, the hosts were extremely responsive and helpful with all the questions and things that came up during the stay. Would definitely recommend and stay again if we are back in the Keys.

The place was exactly like the pictures. On the water and not far from old town key west. Michael was very responsive and gave us all the information we needed for check in and made sure we were able to check in during a certain time and if not other options were available. Would recommend if you want to stay in key west but far enough away from the busy nightlife and have a quiet night in.

Check in/check out was easy! Nice and clean, pool and hot tub area was clean and the pool was nice and warm. We will definitely be check CoolVacay's properties for our next vacation.