Waterfront vacation rentals in Big Pine Key

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Popular amenities for Big Pine Key waterfront rentals

Waterfront apartment rentals

Superhost
Apartment in Key Colony Beach
4.85 out of 5 average rating, 110 reviews

Beachside Unit 22 - Private Beach on Atlantic

JamesRating, 5 stars4 days ago
Place was nice and peaceful. We enjoyed the down time. Enjoyed laying on the beach and soaking up the sun. Only thing I can say negative is the tide was high and had lots of seaweed so u couldn’t get in the water but that’s out of ur control. Definitely somewhere we will return too in the future.
Top guest favorite
Apartment in Key Largo
4.99 out of 5 average rating, 146 reviews

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths

EmmaRating, 5 stars1 week ago
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.
Guest favorite
Apartment in Marathon
5 out of 5 average rating, 19 reviews

#1 Island Hideaway 89 - OCEAN FRONT

BrianRating, 5 stars1 month ago
Rhonda's place is terrific! Lovely location with full water views. Pool was excellent. The home was very comfortable, clean and convenient to restaurants and stores. Would definitely rent again.
Superhost
Apartment in Key West
5 out of 5 average rating, 4 reviews

Hyatt Windward Pointe! Great Location!

MelissaRating, 5 stars1 month ago
Beautiful place with a well stocked unit…close enough to all the places we wanted to visit, yet far enough away for a quiet, relaxing day. We loved the area and our stay here. Thank you, Chris.
Guest favorite
Apartment in Key Largo
4.79 out of 5 average rating, 145 reviews

Escape to the Seaside!

CarlyRating, 5 stars3 weeks ago
Perfect spot for a long weekend beach getaway! This was our first time visiting the Florida Keys, and we loved being right on the water with a small beach area to ourselves. The space was ideal for our group of friends, and the location was great—close to local bars and restaurants, some within walking distance or just a short drive away.
Top guest favorite
Apartment in Marathon
5 out of 5 average rating, 5 reviews

Ocean Side Paradise Awaits!

JesiRating, 5 stars1 month ago
Condo was exactly as pictured. Beautiful resort and everyone very friendly onsite. Great location and close to lots to do. Cannot wait to book again.
Superhost
Apartment in Key West
5 out of 5 average rating, 4 reviews

Henry's Penthouse On The Ocean

LindaRating, 5 stars4 months ago
We arrived early on the day of check-in, and because previous guests has left early, we were able to check in first thing in the morning! Henry happened to be in Key West, working around his property, so he very kindly gave us a full tour of the apartment, the parking area, the grounds, pool, and beach. The apartment is whimsically decorated with pastel colors to fit the Key West vibe, and has lots of cute details. Amazingly, all the small appliances, dishes, glasses, and tableware are in the pink/rose colored family. Literally every appliance is pink (Cuisenart, coffee maker, toaster, Keurig, blender, tableware, and more). It gave the place a unified cozy feel. The living room is spacious, with lots of couch room for a family to watch TV together. The kitchen is eat-in, and the bathrooms and bedrooms are super nice. We felt very at-home in Henry's place, and appreciate the details he provides about checking in, keys, garage parking, etc. We had a great time.
Guest favorite
Apartment in Tavernier
4.95 out of 5 average rating, 194 reviews

Boho FL Keys Condo

LisaRating, 5 stars4 days ago
Beautifully decorated, very clean, well stocked, easy to find, and centrally located

Waterfront house rentals

Top guest favorite
Home in Key Colony Beach
5 out of 5 average rating, 73 reviews

Dock, Beach Club, January avail., tennis, golf

Mary KayRating, 5 stars1 month ago
We loved our stay at Jeffery's house. It is spacious and very comfortable. My husband appreciated the proximity to the pickleball courts - we could see them from our bedroom windows- and my son enjoyed fishing off the dock. The upper suite was wonderful for privacy and quiet when the older kids stayed up later than the adults. Jeffery was super helpful and responsive. We would love to stay here again!
Superhost
Home in Marathon
4.81 out of 5 average rating, 36 reviews

Luxury Waterfront Retreat with Dockage & Pool

KathrynRating, 5 stars1 week ago
We had a wonderful family vacation at Naomi’s place. The place was perfect for our family of 4. There was so much to do to keep our active family busy. The house was well stocked with everything you may need for meals. Host was very responsive and helpful throughout our stay. We rented a boat and the dock was perfect for storing. We are looking forward to staying here again on our next visit to the keys!
Superhost
Home in Marathon
4.83 out of 5 average rating, 23 reviews

Pelican Inn

BillRating, 5 stars2 weeks ago
Our family of four stayed for a week in mid April and had a great time. Karen’s place was convenient to access all of our activities. We fished, went snorkeling, and visited pigeon Key. Lots of good restaurant options within just a few miles. We would definitely stay there again.
Superhost
Home in Islamorada
5 out of 5 average rating, 6 reviews

A Pirates Great Escape ~ 3bed/2baths Ocean View B

GretchenRating, 5 stars16 months ago
Enjoyed the open space this rental had to offer. Very clean. Great views. Quiet location. Beds were very comfortable. The binder with all of the rentals information and suggested restaurants and things to do was very helpful!
Guest favorite
Home in Key Colony Beach
4.91 out of 5 average rating, 135 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

NicoleRating, 5 stars2 weeks ago
We didn't know anything about Key Colony so based our reservation strictly on reviews and price. Well worth every penny that was spent. What a wonderful tropical getaway! Can't wait to visit the Keys again with my 4 children and husband. If you're looking for a great place to spread out and enjoy family this should be your rental.
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Paradise Palms~ Open Water Views w/ 40' Dock, Pool

BrianRating, 5 stars2 weeks ago
This home and location are exceptional!!! Everything about it exceeded our expectations, and I wouldn’t hesitate to rent a vacation home from Coco Plum again. It is expensive, but when you look at all you get and the location, it’s actually a bargain. The owner really has an exceptional home! Our family had a great time, and we will be back next year. Thank you!
Guest favorite
Home in Key Colony Beach
5 out of 5 average rating, 26 reviews

Easy Ocean Access 30' Dock House Pool Cabana Club

BookerRating, 5 stars1 week ago
The hosts were so accommodating and friendly. The space was newly remodeled with excellent quality and style of workmanship. It was also immaculately clean and incredibly well stocked. Our family of five (three young adult boys) was always comfortable. The hosts thought of everything you could want on vacation. They worked with us to make sure we had a place to dock and use our wave runners, there was outdoor dining and grilling space, complete with a filtered ice machine and an outdoor chest fridge for any fishing, a beautiful spot overlooking the canal, a pergola over the sitting area to provide extra shade, and the house itself was gorgeous and well appointed with plenty of space. We’d love to visit again!
Top guest favorite
Home in Key Colony Beach
4.98 out of 5 average rating, 104 reviews

Waterfront House with 37 ft Dock & Cabana Club

CatherineRating, 5 stars3 weeks ago
Jorge was an excellent host! The home is beautiful, right on the canal. It is very well stocked with thoughtful amenities. We particularly appreciated the paddle board/kayaks, beach chairs/umbrella, and well-supplier kitchen. We would recommend his home to anyone visiting the keys!

Waterfront condo rentals

Guest favorite
Condo in Key West
4.97 out of 5 average rating, 73 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

LesleyRating, 5 stars3 weeks ago
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.
Superhost
Condo in Tavernier
4.87 out of 5 average rating, 150 reviews

Reel Large END Unit in Ocean Point Suites

JohnRating, 5 stars1 week ago
Nice, clean and quiet place. pool was nice. Nice view off the balcony is of the mangroves. Beach area is nice but pretty rocky once you get into the water.
Guest favorite
Condo in Key Largo
4.87 out of 5 average rating, 122 reviews

Kawama Breeze

JosephRating, 5 stars2 weeks ago
The host included touches of home which made the condo an even better value for our stay. For example, a few dish washer pods and laundry pods were included so we could avoid buying our own. Everything was spotless clean upon our arrival, along with the place being exactly as pictured and described. Bonus that the complex play area was nearby for my young kids (not too close to be noisy though). We are already talking about coming back and trying to stay at this location again. The location is great being so close to many activities and restaurants while feeling secluded and comfortable. The host is very responsive and accommodating for all requests we had. We definitely highly recommend this host and this property!!
Guest favorite
Condo in Tavernier
4.94 out of 5 average rating, 141 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

BrianRating, 5 stars3 weeks ago
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
Top guest favorite
Condo in Tavernier
4.98 out of 5 average rating, 196 reviews

Ocean Views at Ocean Pointe

PattyRating, 5 stars1 week ago
We had a fantastic stay at this condo in Tavernier! The location was ideal—close to everything we wanted to see and do in the Keys. The unit was clean, comfortable, and well-stocked, with a beautiful view of the ocean that made every morning feel like a dream. The host was extremely responsive and made everything easy from check-in to check-out. Highly recommend this place—we’d love to come back!
Guest favorite
Condo in Tavernier
4.99 out of 5 average rating, 106 reviews

Modern and Coastal Ocean Pointe 2307

LeahRating, 5 stars2 months ago
Exactly as pictured! Beautiful getaway in the Keys! It was very clean, even up to my picky healthcare expectations! Had everything we needed! A few more towels would have been great but we made it work. Kitchen stocked with all we needed. It was great to know what amenities and products were included and how much up front. The recommendation book was awesome! Beds were comfortable, all tvs worked well. Nice to have cable included too! The pool was absolutely beautiful, especially at night. Very clean facility outdoors as well. The beach area was probably the only disappointment, and out of their control. Just wasn’t as sandy etc. as we thought from pictures. Still very nice. It was also so nice to have a door code and not worry about a key. The neighborhood was welcoming too and safe to go for a morning run. All in all we would highly recommend this condo for your Keys vacation, family or couple! Our family of 6 fit :). Thanks for a great home away from home!
Guest favorite
Condo in Tavernier
4.84 out of 5 average rating, 152 reviews

Bright & Sunny Suite w/ Magnificent Ocean Views

AlexRating, 5 stars1 week ago
Beautiful views, well appointed condo, great amenities and location is very convenient.
Guest favorite
Condo in Tavernier
4.94 out of 5 average rating, 124 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

ChrisRating, 5 starstoday
Can’t say enough good things about Nicole’s place. Everything was as described and so much more than we expected. Close to everything you need. Great food, fishing dolphin encounters, sand bars and so much more. Can’t wait to come back!!!

Quick stats about waterfront rentals in Big Pine Key

  • Total rentals

    140 properties

  • Nightly prices starting at

    $110 before taxes and fees

  • Total number of reviews

    2.5K reviews

  • Family-friendly rentals

    120 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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