
Holiday rentals with outdoor seating in Big Pine Key
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Top-rated Holiday Houses with Outdoor Seating in Big Pine Key
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Popular amenities for Big Pine Key outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Cancellation Deal: 08/02 thru 08/09
The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie

May availability 70ft Dock, Near Beach VACA23-16
Jeffrey’s place was a wonderful landing pad for our week in the keys. Lots of small details thought out that add up to a relaxing stay. (Beach towels, coolers and beach gear, family games, etc.) Kids didn’t wanted to live there forever!

Newely Renovated 3/2-private pool/dock/cabana club
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!

Beachfront Villa - Florida Keys
We had a great stay at Loretta’s place. The location offered a good jumping off point to explore the keys. The beach nearby along with canal access and kayaks was a huge plus. The garden area was nice though the mosquitos were intense. The place accommodated our group of 7 ppl well and everything was clean and well furnished. Overall, the place worked great for our group and we’d stay again!

Waterfront FL Keys Cottage @ Venture Out
Great location, easy access to everything, lots of amenities on the community.

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV
We had a wonderful time staying at Tim’s place! He was an excellent host who was always available if I had a question. The house is in a beautiful location. We enjoyed sitting on and fishing off the dock. The house had everything we needed for a fantastic stay and a very enjoyable vacation. I can’t say enough good things about our experience at the home. We were able to meet Tim and he was a lovely host. Thank you for a great vacation! We hope to come back in the future!

Waterfront Venture Out Home
Just as described. Would totally stay again.

Private Pool! Luxury Paradise Pointe, Pet Friendly
Amazing Stay in the Florida Keys! We had an absolutely incredible time at this home in the Florida Keys! Everything about our stay was perfect. The house was clean, comfortable, and had everything we needed for a relaxing getaway. The highlight was definitely the pool — it was beautiful, well-maintained, and the perfect spot to unwind after a day of exploring. The outdoor space was peaceful and made it feel like our own private paradise. Loved the tv out by the pool! We couldn’t have asked for a better place to stay. The location was great, the home was even better than expected, and we left feeling completely refreshed. Highly recommend and would definitely stay here again!
Apartment rentals with outdoor seating

New Deluxe Duplex Unit, 2 Queen Beds, Unit H-5
The place was nice and very clean, easy to find, and had everything we needed, the area is very nice, you can see a lot of deers around it, we really love it. I would highly recommend this place.

Beachside Unit 22 - Private Beach on Atlantic
Very nice condo in key colony beach, affordable, great stay for a family. Clean rooms, nice pool, nice private beach area, will bring family down again.

Honeymoon Hideaway, King bed, Private Deck & Spa!
This was our first time traveling to Key West and we weren’t sure what to expect. I can’t say enough great things about Center Cottage Inn. They went above and beyond our expectations and it was the perfect place to experience a lot of the wonderful things the island has to offer. The cottage we stayed in was fully equipped for all of our needs and was tiny in the best way. It had a lot of great storage, ample towels (both for bathing and the pool), fully stocked kitchen (we opted to make our own breakfast each day), and lots of thoughtful details like a portable speaker, bug spray, charging ports and more. Naomi was super responsive and helpful. We were able to leave our bags on the premises as our departure flight wasn’t until late afternoon. This was a game changer as we were able to enjoy our last day without carrying luggage around. If you want to feel like locals this is the place for you.

At Mine | Key West Suite steps from Duval Street
This is a secret little gem of a place to find! Quiet, perfect walking distance to everything! Very thankful I found this place. Everyone was friendly! The pool makes you feel like you’re in a tropical jungle. The setting is just right! I would recommend this place to everyone. We will definitely be back.

Studio Near Downtown - The Bartlum
Conveniently located spot that is walking distance to Duval and all the nearby restaurants and sights!

Duval Street Suites full kitchen, free parking, &
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

Duval Balcony - Suite Mischief
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!!!

Beachfront Condo w/ Ocean Views in Marathon
This was our first family trip to the Keys and this location in Marathon was ideal! The condo was welcoming, beautiful and spacious for our family of 3. The balcony was our favorite place, which overlooked the pool and the seashore. The beach was lovely for shorter walks and just "being" with the ocean. Fun seashells & hermit crabs at low tide! Lots to do in the area -- definitely hoping to return next year. Mike was fantastic host & super helpful with questions.
Condo rentals with outdoor seating

La Dolce Vita, Old Town Steps to Duval! 3 blks bch
Right next to Duval Street, easily walkable to major attractions, restaurants, bars.. Host was super responsive, friendly, and really worked with us on anything we needed.. Great place!

Villa 5027 on Duck Key BOAT SLIP available
The place was perfect. The patio views were amazing to just sit and watch the sunset. The marina across the street was very convenient to launch our boat from. Very peaceful location. Angler and ale restaurant across the street was delicious

Oceanfront 3 bed condo Ocean Edge w/ optional slip
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!

Condo de Paradise/Salt Water Pool/Boat Dock
We are absolutely in love with this place. The views are gorgeous. the grounds were immaculately groomed. There are so many colorful trees and flowers. The pool is slightly heated, which is perfect. Everyone we met was so nice and helpful with recommendations. We got to see the jets fly over a few times, so cool. The kitchen has everything you need to prepare meals and snacks. The beds in both rooms are very comfortable. We hope to stay here again in the future.

Affordable Beachfront Luxury Condo Sleeps 6
Traci’s condo was great in every way! Everything was very clean and the view was amazing. We could enjoy watching the turquoise water and swaying palm trees from almost every room – both bedrooms, living room, kitchen, dining area, or relaxing on the large balcony. Some of the furniture is different in the photos, but my group agrees it is even better now than what you see. Having our own parking space in the garage was much appreciated, too. Traci responded quickly; clear check-in instructions. We would definitely stay here again.

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access
We had a great stay at Jennifer’s condo! It was clean, well-appointed, and had beautiful views of the harbor. The location was perfect—just a short drive to all that Key West has to offer. Jennifer was a proactive host and kept us well informed throughout our stay. Highly recommend!

A Perfect Getaway
We had a wonderful visit in Key west. The place was very clean, close to everything. We enjoyed this place very much and would rent it again. Thank you so very much. Sue and Dave Hopper.

Fully renovated 2/2 bath condo w/ shared pool!
This listing was everything and more! The space was very clean, and provided all of the necessary amenities. As far as location…top tier. All the major attractions and beaches were a short 15 minute drive. Chris was responsive when I reached out. Truly a gem, and I would recommend this space again and again.
Quick stats about holiday rentals with outdoor seating in Big Pine Key
Total rentals
110 properties
Nightly prices starting at
$100 NZD before taxes and fees
Total number of reviews
2.6K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
60 properties have a pool
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