
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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Holiday House Rentals with Outdoor Seating

Islamorada Cay Home. Elegant home
The outdoor space is absolutely fabulous. The heated pool was enjoyed every day. The property is on the corner of two canals that had pretty clean water. We met several manatees who graced us with their presence often. Fishing was not great during the month so our fishermen were rather disappointed. The interior was very pleasant and cooking was easy. The entire third floor is the master sitting room, bathroom and bedroom. The only drawback for me personally is that the master bathroom is an "open concept " design which left me without a sense of privacy. Isa was extremely helpful and responded quickly with our questions. Thank you Isa!

Waterfront Home 37.5-ft dock, Cabana Club Included
We loved our stay! The house was super clean and the back patio was beautiful. We loved the back canal area and saw lots of very cool wildlife and enjoyed fishing right there. Having the kayaks to use was also great. Beds were very comfy and the rooms were spacious. The house had everything we needed. We loved the key colony area. The cabana club was a great space and the house is in walking distance to Sunset Beach, which was beautiful. The whole area is super close to fun things to do and great restaurants. We would absolutely stay here again!

Lower Keys Paradise
Great place to stay. It’s a house in a community with a lot of activities available. There’s an extra $125 fee for that, but it’s worth it.

Waterfront Anchor House with Boat Basin & Ramp!
Epic Trip. My family and friends felt right at home, and to be honest I could have just stayed. This was by far our best trip ever and will want to do it again. So much fun, and was a treat to spend so much time on the boat in the water and just get in. Great setup. Everyone we met from Kiki's, Marina, Tackle Shop and other staying in Cozy Coves were so nice. Special shout out to Walt, who was too cool and very welcoming. Little Torch Key is my kind of speed, slow, not too crowded and amazing scenery. Thank you so much for a lifelong memory that we won't ever forget. Island Time!!!!

Beachfront Villa - Florida Keys
The location was great, the house was comfortable and clean. The dock and canal were wonderful. Loved having our boat so close and loved the manatee that came to visit us. Overall very nice home and would highly recommend. Loretta had good communication on check in and info. Thank you and we look forward to returning!

Dream Vacation KCB Marathon with private pool !
Alfonso is a very responsive host who provided clear details, local recommendations (multiple of which we used), and provided a place in a great location. Neighbors are friendly. Place was clean. Perfect for our family with a 14 and 6 year old.

Kittyhouse on Catherine, Tropical Pool, Parking
Thank you for sharing your beautiful home. We appreciate your wonderful suggestions and thoroughly enjoyed our dinner at El Siboney restaurant. Unfortunately the rain kept us from using the pool but we still had a fantastic time.

Cary’s Oceanside
We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.
Apartment rentals with outdoor seating

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths
Beautiful home in a beautiful location. Norma is a fantastic host, so helpful and friendly with lots of recommendations some of which we tried and loved. We would definitely stay again and recommend.

Studio Near Downtown - The Bartlum
Our first time using Air B&B. My wife loved the experience and location. I liked not having to drive. Parked the car and walked everywhere. Would definitely book again. Thanks for being great hosts!

Key's Cottage Escape
Good place with private parking. Checkout is too early (9am) but we managed to make it

Duval Street Suites full kitchen, free parking, &
Exactly as listed. Megan was very helpful and responsive. You are right in Duval street. If you are coming for a few days, this is the place to stay at.

Boho FL Keys Condo
Beautifully decorated, very clean, well stocked, easy to find, and centrally located

Duval Balcony - Suite Mischief
Had a pleasant stay at Thomas place. Great location, lots to do and close distance to everything. Suite was very big and it was nice to have a private balcony. Bedroom and bed are a great size. Wish I could’ve stayed longer, definitely planning a future stay here!

Beachfront Condo w/ Ocean Views in Marathon
I had to call Mike because a breaker tripped and we could not find the breaker box. He responded immediately and directed us to the correct location. He also took the time to ask if we were enjoying the condo and if there was anything we needed.

3. Oceanside Retreat with Canal Access, Key Largo!
I have so many great things to say and don't know where to begin. It's everything I wanted and more! we'll managed/great area! You will love it! I love how modern, very functional and they communicate well! I also stayed cause the pricing was not outrageous. I will stay there again if I come back to the Florida Keys!
Condo rentals with outdoor seating

Oceanfront 3 bed condo Ocean Edge w/ optional slip
Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.

Your Happy Place - Oceanfront
Beautiful and peaceful place to stay, having the pool was amazing for days we didn’t want to do the beach. Restaurants around are amazing and Sandra gives wonderful recommendations.

2BR - Key Largo Sunshine Getaway
Great place for a family. The pool and beach were ideal for kids and the little tiki bar was great for us. The surroundings were lush. We would stay here again.

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
The unit is just like the photos and was very comfortable! John was helpful and helped make for an enjoyable stay! Would happily stay here again

Waterfront Spacious Condo Key Largo #4, 10% Off 7+
Javier’s place was as expected. The balcony over looking the canal was awesome. We saw lots a cool fish, a turtle and even a manatee swim right up. The property abuts dolphin plus, where you can swim with dolphins and there is a cute coffee trailer Cuppacobanna situated in the parking lot, has a great Churro latte. Right across the street is the Fish Market. A hidden gem for sure! Walk right over and you can order at the window and sit on the water or at their outside bar. We walked over to the dock at the market and saw tons of nursing sharks just hanging out. We were in town for a wedding at Dream Bag Resort which was only 3 minutes away. Great location, super convenient. Although beds and everything were super clean, I would suggest new comforters which someone previously stained. Also one back cushion missing from the outside patio chairs. We did not need to cook at all so hard to judge that aspect. Not an over abundance of kitchen supplies but the basics. Great stay!

Light, Bright & Nautical Condo [Ocean Pointe 1211]
We were very happy to stay there as a family of three. The property is convenietly located and easy to find. Check-In process was flawless. As already mentioned the Condo was very clean. Largo is a state of the art renter. We lost our car-keys in the drive way and he immediately contacted us when they were found and could be retrieved at the gate. We were in the Tavenier area for diving and were diving mostly with Conch-Repbulic Divers and Rainbowreef-Divers. Both shops can be reached within minutes. We definately recommend the Condo and Largo and would book the Condo anytime again. There were absolutely NO negatives and we were very happy to stay there.

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"
This was a treasure in paradise for 2 couples to stay and feel completely relaxed. We enjoyed coffee sunrises, a wonderful sunset walk around the marina and we were in walking distance from anywhere we wanted to go in Old Town. Inside the home was a well appointed kitchen that met any cooking need including salt and pepper. It would have been a pleasure to cook but we ended up reheating our leftovers from all the great restaurants we visited. Coffee sunrise and a cocktail in the evening shade overlooking the marina on that beautiful big balcony were highlights of our time there. Thank you from all of us to our gracious host Jennifer. Laura, Neil, Rich and Deb

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Great little place for our family of 4! Very clean and the location was perfect for us. Would definitely stay again!
Quick stats about holiday rentals with outdoor seating in Big Pine Key
Total rentals
110 properties
Nightly prices starting at
$92 AUD 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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