
Beachfront vacation rentals in Big Pine Key
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Top-rated beachfront rentals in Big Pine Key
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Popular amenities for Big Pine Key beachfront rentals
Pet-friendly beachfront home rentals

Key West Luxury Houseboat at Yacht Club Resort
We stayed in two smaller house boats while we were there before brads. Rectangular shaped single stories with a flat roof area for lounging. They were beautiful.. but unstable, uncomfortable, limited in space, no hot water, had to shower 200 yards away, awful mosquitos, no reliable internet, lack of kitchen ability, I’m 32 my wife is 30 and our son was five months. Pretty looking, but miserable. Especially if wind wasn’t below 5mph. Not to mention the toilets had problems on both! When we got to brads house boat Holly Cow! What a difference. What a relief. Multiple rooms, comfortable beds, no issues with hot water or internet or kitchen. The space was excessive. Very comfortable. Needed some TLC inside but overall it was fantastic. Everything worked like a real 2br 3ba home. I will book this boat everytime as long as it lives. Private marina, quiet, great neighboring boats. Private outdoor waterfront recreational areas. 100% best key west experience I’ve had and I go every year.

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!

Spacious lux home, private pool/spa, 80' dock
The house was exactly how it was described online. Everything was well marked. Lots of stuff to do at the home. Very spacious and well maintained. There were only 7 of us, so lots of extra space. The pool is on the perfect side so your not blasted with the late afternoon sun. However, there is a huge umbrella in case it is needed. Kitchen is fully stocked so nothing was needed. There is a BBQ grill as well as a flat top which is nice for outside cooking. The only thing I would recommend is to bring your own pillow if your a particular pillow person (we love our feather pillows), house pillows were not feather ones. If you rent here and have a boat definitely go to the Sombrero Lighthouse to snorkel. Never saw so many fish in one place. The Conch Cafe and Coast to Coast pizza are both great food restaurants and walkable from the home. Publix is so close it was a daily visit. Truly enjoyed the week stay!!!!!

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach
Great place to stay for family vacation or guys fishing trip. Plenty of dock space to park the boat and easy access to the Atlantic. House is clean and all amenities worked as they should. Would definitely recommend to a family or friend. Mary was a great host who provided all information without even requesting it.

Waterfront w/pool and hot tub
Rachel’s home is so beautiful and relaxing. The area is perfect. We had such a nice time! My daughter has pet allergies, and she had no issues at all the two days she joined us because it was so spotless and clean.

Vibrant Beachfront Villa
Location view and everything was wonderful, we will definitely be back again! 😊

NEW: Vaca Cut with 60' dock, 4br-4ba, 2 kitchens
Beautiful home, we come down to fish and dive, couldn't be a better location to keep our boat and get offshore quickly. Everything is within 5 minutes of the home and the bait shop and ice is at the end of the street. Super convenient. Public boat ramp is a 5 minute boat ride away. Definitely recommend

Coco Plum Waterfront Hideaway Home in Marathon
Fantastic stay, and a fantastic host! They went out of their way to make sure we had everything we needed for our stay.
Beachfront home rentals with a pool

Waterfront 35’ Dock,80’ pool,20 min Key West
We had a great stay! House was neat and tidy and in a great location.

Discount Available! 100' Dock, Lots of Amenities!
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.

Sea Turtle Cove
Philip's listing described the place perfectly. Zero unexpected surprises and it had absolutely everything to make our vacation super enjoyable. When it comes to location, so much to do in under 30 minutes. Smack dab in the middle when it comes to driving to Marathon or Key West. It was also great to be able to keep a boat right outside and to have a marina as part of the park. Access to great places to fish are 15-30 minutes away.

Beach House, Private Pool & Dock, Gulf Sunset view
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!

Stunning* New* Home Pool in Ocean Breeze Marathon
Susan’s place was exactly as described. The water view from the top deck was a wonderful place to have my cup of coffee every morning. I would highly recommend this place.

Canal/Dock - Cabana Club - Pickleball - Remodeled
Brian’s place was exceptionally clean. We slept great in the beds. Shower pressure was great. We enjoyed cooking on the grill. Kids enjoyed watching Netflix. Saw a manatee in the canal, that was cool. Great location. Felt very safe walking in the neighborhood. Adored the staff at the Cabana club and the great food and service there. Pool was very clean and great to be right on ocean. Cannot fault this rental in any way. Also Brian checked in with us which was a personal touch that was appreciated. Awesome place!!

Boat Dock+King Beds & Cabana Club
Randall's place was amazing! Exactly what we were looking for - beautiful views of the canal with a dock and views on the other side of the house facing the golf course. The sunrise and sunsets were spectacular here and we loved the beach at the Cabana Club. The bed was also extremely comfortable. Roy and Randall got right back to us with any questions we had. The entire stay was perfect. couldn't have asked for more. Thanks so much!!

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Jason’s place was a great place to stay in the keys!! Jason is great at responding great location, clean house only the couch could use a cleaning. It would have been nice if there were trash bags, extra hand soap and extra toilet paper. Other then that it was perfect!!
Private beachfront home rentals

Keysie Does It at Cudjoe Key
We absolutely loved our stay! Our checkin was smooth and flexible. The home was squeaky clean, linens and beds were unbelievably soft and comfortable, and there were more supplies/ amenities in the home than listed. We felt right at home and would love to come back! Absolutely 5 star place!

Florida Keys Oceanside Utopia
We spent an amazing week in the house of Kelly and Shane. The location on the waterfront is unbeatable and the house itself is super convenient, nicely remodeled and has a very cozy feel to it. We spent days in a row fishing from the dock, prepared our catch of the day on the bbq on the terrace, and caught shrimp at night which served as bait for the next day. There are great beaches, restaurants, and all kinds of day trips at hand if you wish to leave the property ;). Kelly and Shane are great hosts, with tons of tips - they clearly love the area and put great effort in the maintenance of the house and dock. They are super quick and easy in their communication and all three of us (me, husband and our 12 year old son) look forward to staying at their property again!

A slice of paradise in the Florida Keys
Wonderful night! Only a few bugs around dusk that left by nightfall. Lots of planes took off from 5-7 PM, but again they stopped by nighttime and not sure that it happens every day. The boat itself was perfect, exactly as described!

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
We had a great long weekend at Alex house! You are provided with a starter kit, so you may need to buy extra supplies if planning to stay in at property. House vibes are very keywest. Winn Dixie very close and Bahia Honda state park was close by and beautiful to spend the day if looking for something to do. Keywest about 40 min drive, easy to get around. Had plenty of blankets, pillows and accommodated 10 of us— we did bring an air mattress which I would recommend as sofa beds are not the most comfortable. Has a beautiful backyard which we spent a lot of time on and yummy walkable restaurant. Plenty of parking. Host was very responsive and checked in with us to make sure check in was smooth.

Moana Hale Paradise #164 - Venture Out, Cudjoe Key
It’s awesome. The additional fees are worth it. The community is great and the commitment to keeping the neighborhood classy is excellent.

P36 - Charming and immaculate 2 Bedroom, 2 bathroo
Great place! Very spacious, nice dock and out door and area to enjoy with the pool! It was nice having a large deep freezer for ice and fish!

Flamingo Palms-Spring discounts-NOW available
Excellent host and great home and location. Fishing from the dock, grill on the patio. Lovely decor throughout the property. Made for an excellent choice for my wife’s milestone birthday celebration and Ramon and Ana made that extra special with a birthday banner. Would visit again travel plans permitting

Luxe Waterfront Keys Cottage- with Jacuzzi
Super nice place to stay. Very comfortable.
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