Beachfront vacation rentals in Big Pine Key

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Popular amenities for Big Pine Key beachfront rentals

Pet-friendly beachfront home rentals

Superhost
A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.
Houseboat in Key West
4.87 out of 5 average rating, 245 reviews

Key West Luxury Houseboat at Yacht Club Resort

GarrettRating, 5 stars3 weeks ago
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.
Guest favorite
The image captures a sandy beach scene with clear turquoise waters. Sunbathers and beachgoers are seen enjoying the sun on the shore, while lush palm trees line the beach. A beachfront villa is visible in the background, enhancing the coastal setting.
Home in Marathon
4.91 out of 5 average rating, 179 reviews

Beachfront Villa - Florida Keys

MorganRating, 5 stars3 weeks ago
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!
Guest favorite
The spacious canal-front home is showcased from an aerial view, highlighting its private pool and lush palm trees. A dock with boat access extends into the water, while comfortable outdoor seating is positioned nearby, creating a relaxed atmosphere for guests.
Home in Marathon
5 out of 5 average rating, 22 reviews

Spacious lux home, private pool/spa, 80' dock

HeatherRating, 5 stars1 month ago
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!!!!!
Superhost
A tiki bar with a thatched roof offers seating along a glass countertop. Two cocktails rest on the counter, with serene water views visible beyond. Boats are docked discreetly along the shoreline, surrounded by greenery and natural light.
Home in Key Colony Beach
4.74 out of 5 average rating, 141 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

MichaelRating, 5 stars3 weeks ago
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.
Guest favorite
A private backyard features a hot tub and a shallow pool, surrounded by tropical greenery. Lounge chairs in teal are positioned nearby, and a grill is placed on the concrete patio. The canal is visible in the background, lined with palm trees.
Home in Marathon
4.94 out of 5 average rating, 35 reviews

Waterfront w/pool and hot tub

TanyaRating, 5 stars1 month ago
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.
Superhost
A shaded outdoor porch features four blue adirondack chairs arranged around a round table, overlooking tranquil water views. The surrounding area is adorned with lush greenery and distant views of a bridge, creating a serene space for relaxation.
Townhouse in Duck Key
4.83 out of 5 average rating, 174 reviews

Vibrant Beachfront Villa

OliviaRating, 5 stars1 month ago
Location view and everything was wonderful, we will definitely be back again! 😊
Guest favorite
A spacious outdoor deck features comfortable seating and a large mural of a marlin. Sunlight reflects off the turquoise water in the canal, while palm trees sway in the gentle breeze, creating a relaxing atmosphere for guests.
Home in Marathon
5 out of 5 average rating, 6 reviews

NEW: Vaca Cut with 60' dock, 4br-4ba, 2 kitchens

BarbaraRating, 5 stars1 month ago
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
Guest favorite
A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.
Home in Marathon
4.94 out of 5 average rating, 103 reviews

Coco Plum Waterfront Hideaway Home in Marathon

KyleRating, 5 stars2 weeks ago
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

Guest favorite
A serene waterway is framed by charming homes, with a white boat bobbing gently at the dock. The sky displays a vibrant sunset in shades of orange and pink, reflecting softly on the calm water, creating a peaceful waterfront scene.
Home in Cudjoe Key
4.98 out of 5 average rating, 47 reviews

Waterfront 35’ Dock,80’ pool,20 min Key West

KimberlyRating, 5 stars2 days ago
We had a great stay! House was neat and tidy and in a great location.
Top guest favorite
An aerial view captures a coastal community surrounded by vibrant blue waters and lush greenery. Boating channels meander throughout the area, leading to nearby homes. A mixture of residential properties and docks is visible, indicative of a relaxed tropical lifestyle.
Home in Marathon
5 out of 5 average rating, 41 reviews

Discount Available! 100' Dock, Lots of Amenities!

DanaRating, 5 stars1 week ago
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.
Guest favorite
An aerial view showcases a large, octagonal pool surrounded by lounge chairs in a gated community. The pool area is bordered by palm trees and overlooks the nearby waterway. Residential homes and vehicles are visible in the background under a bright blue sky.
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviews

Sea Turtle Cove

ThomRating, 5 stars1 month ago
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.
Guest favorite
A private pool is surrounded by a lush tropical garden, featuring tall palm trees and vibrant foliage. The clear water of the pool reflects the sunlight, while stone pathways and colorful blooming plants enhance the natural ambiance.
Home in Marathon
4.95 out of 5 average rating, 60 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

DanielRating, 5 stars2 weeks ago
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!!!
Superhost
A community pool area is surrounded by tropical landscaping. Lounge chairs are positioned around the pool, with a large striped umbrella providing shade. Pool steps lead into the water, and a textured stone surface allows for easy movement. The atmosphere is relaxed and inviting.
Home in Marathon
5 out of 5 average rating, 3 reviews

Stunning* New* Home Pool in Ocean Breeze Marathon

JuanitaRating, 5 stars8 months ago
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.
Top guest favorite
A large outdoor pool is surrounded by palm trees, creating a relaxing environment. Lounge chairs are arranged along the poolside, with a shaded area featuring umbrellas. Steps lead down into a hot tub connected to the pool, inviting guests to enjoy the water.
Villa in Key Colony Beach
5 out of 5 average rating, 30 reviews

Canal/Dock - Cabana Club - Pickleball - Remodeled

ErinRating, 5 stars1 week ago
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!!
Top guest favorite
A large swimming pool is surrounded by palm trees, creating a tropical atmosphere. The pool features a hot tub integrated into the pool area, with comfortable lounge chairs positioned around it. The sky is clear, and sunlight reflects off the water's surface.
Home in Key Colony Beach
5 out of 5 average rating, 22 reviews

Boat Dock+King Beds & Cabana Club

OliviaRating, 5 stars1 week ago
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!!
Superhost
The image displays a spacious swimming pool surrounded by palm trees, with lounge chairs positioned along the poolside. The water reflects the cloudy sky above, and the ocean can be seen in the background, creating a calm and inviting atmosphere for relaxation.
Cottage in Cudjoe Key
4.63 out of 5 average rating, 112 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

Elizabeth CarmenRating, 5 stars3 months ago
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

Guest favorite
An inviting open living area is featured with comfortable seating options, including a large blue sofa and patterned chairs. A flat screen TV is positioned on a wicker stand. A staircase leads to the second floor, and a dining area with a round table and rattan chairs is visible.
Home in Cudjoe Key
5 out of 5 average rating, 16 reviews

Keysie Does It at Cudjoe Key

MeganRating, 5 stars3 months ago
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!
Guest favorite
A spacious outdoor area features a well-maintained dock alongside calm waters. Luce lounge chairs are arranged for comfort, with palm trees offering shade. The exterior of the duplex is visible, showcasing large windows and a patio area adjacent to the dock, enhancing the waterfront experience.
Home in Marathon
4.94 out of 5 average rating, 34 reviews

Florida Keys Oceanside Utopia

LisetteRating, 5 stars2 months ago
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!
Superhost
A serene view of a tranquil waterway is presented from the deck of the floating house. Two black chairs are positioned on the wooden deck, facing the peaceful water. Lush green trees frame the scene, with sunlight reflecting off the calm surface.
Houseboat in Key West
4.71 out of 5 average rating, 173 reviews

A slice of paradise in the Florida Keys

CarmenRating, 5 stars2 months ago
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!
Superhost
Home in Summerland Key
4.59 out of 5 average rating, 83 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

SarahiRating, 5 stars4 weeks ago
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.
Guest favorite
A canal-front dock features colorful adirondack chairs positioned for scenic views of the water. The surrounding area includes nearby houses and a clear blue sky, enhancing the outdoor experience. The dock provides direct access to the water, ideal for boating activities.
Home in Cudjoe Key
5 out of 5 average rating, 6 reviews

Moana Hale Paradise #164 - Venture Out, Cudjoe Key

anthonyRating, 5 stars2 months ago
It’s awesome. The additional fees are worth it. The community is great and the commitment to keeping the neighborhood classy is excellent.
Top guest favorite
A private pool is situated beside a spacious deck, surrounded by tropical plants and palm trees. Comfortable lounge chairs are placed near the pool, and stairs lead to the upper level of the stilted structure. The area offers direct access to the canal.
Home in Marathon
5 out of 5 average rating, 14 reviews

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

BradleyRating, 5 stars2 weeks ago
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!
Top guest favorite
A boat is docked beside a light blue cottage, featuring large windows that reflect on the water's surface. Lush palm trees surround the property, enhancing the tropical atmosphere and offering a serene view of the canal.
Home in Marathon
4.98 out of 5 average rating, 47 reviews

Flamingo Palms-Spring discounts-NOW available

LaurenceRating, 5 stars1 month ago
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
Guest favorite
A rattan chair with a rounded backrest is positioned against a striped wall. The chair displays decorative pillows and a light throw blanket. A small side table holds a lamp and a decorative item, contributing to a relaxed atmosphere.
Home in Marathon
4.92 out of 5 average rating, 50 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

MaxsenaRating, 5 stars1 month ago
Super nice place to stay. Very comfortable.

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