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Waterfront holiday rentals in Summerland Key

Find and book unique waterfront accommodation on Airbnb

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Popular amenities for Summerland Key waterfront rentals

Waterfront apartment accommodation

Superhost
Apartment in Islamorada
5 out of 5 average rating, 3 reviews

Ocean View Duplex Penthouse | Pool | Vista Two

AnneRating, 5 stars3 months ago
Beautiful, very clean property with a fantastic location. Excellent proximity to snorkeling, restaurants and other local attractions. Short stroll to excellent walking path that takes you along route 1 with amazing morning views of the beautiful water. Great views all around, in fact. Plenty of soft, plush towels and similarly luxurious bed linens. We had a wonderful family vacation staying at this property.
Guest favourite
Apartment in Marathon
4.93 out of 5 average rating, 14 reviews

*NEW* Sea La Vie - Pool & Beach

MargaretRating, 5 stars4 weeks ago
We just spent 6 days at Yuni's airbnb. Our family of four(all adults) could not have been happier with the peace and quiet this place offered us. The private beach and pool had plenty of chairs and umbrellas. We loved the balcony overlooking the pool and beach. We enjoyed how close it was to Havanna Jack's for a quick bite to eat and drink. Yuni's place was exceptionally clean. Plenty of bath towels and beach towels. The kitchen was fully stocked with all of our needs. She quickly responded to our questions and our needs. Yuni is one of the best hosts we have had throughout the years of using airbnbs. We definitely will go back!
Superhost
Apartment in Key Colony Beach
4.84 out of 5 average rating, 115 reviews

Beachside Unit 22 - Private Beach on Atlantic

JamesRating, 5 stars3 weeks ago
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.
Top Guest favourite
Apartment in Marathon
5 out of 5 average rating, 20 reviews

#1 Island Hideaway 89 - OCEAN FRONT

SamanthaRating, 5 stars3 weeks ago
It was the perfect location that we wanted away from a high tourist area. The neighbors were very nice and welcoming. Everything was clean and beautiful. I would stay here again! It was perfect for us exploring both the southern and northern keys and beaches since it's about middle of the 2. Loved it!
Guest favourite
Apartment in Islamorada
4.99 out of 5 average rating, 68 reviews

Hidden Gem Islamorada | 1st Floor

AngelaRating, 5 stars1 week ago
We had a great stay here with our kiddos. The Hidden Gem had everything we needed for a relaxing and fun stay. Close to everything - a great middle keys location. Host sent several texts checking on us throughout our stay. We saw so many cool fish right at the back of the property on the sea wall - barracuda, grouper, parrot fish, Angel fish, and crabs to name a few. We hope to visit and stay again soon!
Top Guest favourite
Apartment in Marathon
5 out of 5 average rating, 12 reviews

Best Catch on Grouper LN at Ocean Isles

WilliamRating, 5 stars2 months ago
Loved it so much! What a beautiful place to stay you won’t be disappointed! Frank was an amazing host and very helpful and responsive! Would come back!
Superhost
Apartment in Marathon
4.86 out of 5 average rating, 51 reviews

Little Venice in Marathon (in the Beautiful Keys)

AlisonRating, 5 stars1 month ago
We (two couples) enjoyed a great week here. Being on the canal was nice, outside sitting spots were great. The house had plenty of cooking supplies needed. Was a tad bit smaller than I expexted, but worked out just fine. Remember to bring your shampoo, body wash etc as it's not provided. Comfortable and bright, was quiet even with boats going by. Would definitely stay here again!
Guest favourite
Apartment in Marathon
4.97 out of 5 average rating, 62 reviews

Dock POOL Kayaks Bikes Beach2mi WalkToStores

jennifer Rating, 5 stars1 month ago
My husband, myself and 3 adult children stayed for a week. Place was super well equipped with everything imaginable. Very Spacious inside and out. Danielle was great at answering any questions we had. It was an amazing family vacation and will definitely rent again. - Jennifer

Waterfront house rentals

Top Guest favourite
Home in Marathon
5 out of 5 average rating, 18 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars2 weeks ago
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!
Superhost
Home in Cudjoe Key
4.85 out of 5 average rating, 52 reviews

Keys getaway

JamiRating, 5 stars2 months ago
We were there to celebrate my husband's 50th birthday. The master bed, pillows and linens were very comfortable. The screened in porch with plenty of comfortable seating was our favorite amenity of the property. We hope to rent there again when we are back in the area. Very comfortable and very clean. 😁
Guest favourite
Home in Cudjoe Key
4.92 out of 5 average rating, 24 reviews

Pelican's Roost, Waterfront comfort at Venture Out

PamRating, 5 stars2 months ago
we totally enjoyed our stay. the home is spacious and has everything you would want or need for your stay. loved the screened in porch area! thank you!!!
Guest favourite
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.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 26 reviews

Million Dollar View

JohnRating, 5 stars1 month ago
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.
Superhost
Home in Cudjoe Key
4.63 out of 5 average rating, 166 reviews

Ocean Front Home in Great Location

HaroldRating, 5 stars2 weeks ago
This booking was great for what we needed, thank you to the responsive hosts and pet friendly house that made our vacation that much better.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars3 weeks ago
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.
Superhost
Home in Cudjoe Key
4.83 out of 5 average rating, 66 reviews

Waterfront Venture Out Home

CaseyRating, 5 stars1 month ago
Just as described. Would totally stay again.

Waterfront condo accommodation

Guest favourite
Condo in Key West
4.97 out of 5 average rating, 74 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

BrianRating, 5 stars2 months ago
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!
Guest favourite
Condo in Key West
4.95 out of 5 average rating, 39 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

Lori Rating, 5 stars1 month ago
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.
Top Guest favourite
Condo in Duck Key
5 out of 5 average rating, 38 reviews

Oceanfront and Sunrise Views!

StephenRating, 5 stars3 weeks ago
We had an amazing stay in this wonderful Condominium! The host was absolutely fabulous - super responsive, friendly, and made sure we had everything we needed. The apartment itself was clean, comfortable, and perfectly located. The whole experience was top-notch, and we highly recommend this place to anyone looking for a great stay. Thanks again to the host for making it so special!
Superhost
Condo in Key West
4.85 out of 5 average rating, 156 reviews

Anchor Drop modern elegance upgrades throughout vi

MoiraRating, 5 stars5 days ago
This was a great condo for 5 of us! PROs- Everything was so nice and clean. The owners are super organized with labeling on sheets, pillows, games, pool toys, etc all clearly marked in bins. The kitchen was well equipped, even though we didn't use it much. The sitting area around the TV was perfect and plenty of room for everyone. The master shower is huge and the bathrooms were very clean. We loved the large balcony. The pool was so nice and plenty of room and chairs, very well maintained. Communication with the property management company was pretty good, although it was more than 12 hours response time on one of the questions we had. They were very helpful and available on a Friday night when we were trying to access the TV and had questions on how to connect, which was great since it was a weekend. CONS- the condo is not situated very close to the Old Town area or restaurants. We took ubers and had a car, so it didn't really bother us. I would definitely book this place again!
Superhost
Condo in Key West
4.87 out of 5 average rating, 202 reviews

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

MickeyRating, 5 stars4 days ago
We recently stayed here with our family and absolutely loved it! The location was unbeatable — right on the harbor with stunning ocean views and easy access to the water. Mornings were peaceful and beautiful, and in the evenings we enjoyed live music from a nearby restaurant, which added such a fun, local vibe. Everything we needed was just a short walk away — restaurants, grocery stores, a tennis court, and a lovely park. We especially enjoyed evening walks together as a family — the area felt safe, vibrant, and welcoming. This stay was the perfect combination of relaxation, convenience, and charm. We’re already looking forward to coming back!
Guest favourite
Condo in Marathon
4.95 out of 5 average rating, 43 reviews

2-story condo w/ panoramic bay views and balconies

LisaRating, 5 stars2 months ago
We live Marathon and this condo is in the perfect location and minutes away from shopping, restaurants and activities.
Top Guest favourite
Condo in Marathon
4.96 out of 5 average rating, 103 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

AlexRating, 5 stars3 weeks ago
Absolutely perfect for a honeymoon getaway, quiet perfect amount of space for us, the set up was great with 2 bathrooms and a huge walkin closet, the couches were super comfy, the TV was big enough to see from across the room, we enjoyed everything about it. Got to meet some of the neighbors and they were all very welcoming and enjoyed talking to them. Scott had some great local recommendations and we enjoyed everything.
Top Guest favourite
Condo in Marathon
5 out of 5 average rating, 20 reviews

*NEW* Private Beach, pool & fully loaded kitchen

JamesRating, 5 stars1 month ago
Our first time visiting the Keys and Celia’s place made it wonderful! Located in a very nice, quiet, and safe community her condo is like new and so well cared for. Perfect size for our two couples. The decor and furniture is very nice, bright and clean. Had all the amenities we needed and then some. We enjoyed the heated pool everyday and the private beach was nice for a more natural experience. The furnished patio had a great view of the pool and ocean. Celia is a wonderful host! Very helpful and a great communicator.

Quick stats about waterfront rentals in Summerland Key

  • Total rentals

    160 properties

  • Nightly prices starting at

    $62 AUD before taxes and fees

  • Total number of reviews

    2.9K reviews

  • Family-friendly rentals

    130 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with a pool

    130 properties have a pool

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