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Waterfront vacation rentals in Summerland Key

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Summerland Key waterfront rentals

Waterfront apartment rentals

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.
Superhost
Apartment in Marathon
4.83 out of 5 average rating, 18 reviews

Seaside Villa~ Charming Beachfront Condo w/ Pool!

DeborahRating, 5 stars15 months ago
The location was amazing. The house was dated and needed some updates in the kitchen and bathrooms. The carpets were in need of replacing. Can't beat the location.
Guest favorite
Apartment in Marathon
4.93 out of 5 average rating, 14 reviews

*NEW* Sea La Vie - Pool & Beach

MargaretRating, 5 stars1 month 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, 116 reviews

Beachside Unit 22 - Private Beach on Atlantic

JamesRating, 5 stars4 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 favorite
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!
Top guest favorite
Apartment in Marathon
5 out of 5 average rating, 5 reviews

Ocean Side Paradise Awaits!

JesiRating, 5 stars3 months 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 Marathon
4.87 out of 5 average rating, 52 reviews

Little Venice in Marathon (in the Beautiful Keys)

KellieRating, 5 stars2 weeks ago
This is our 2nd time staying here. Great location and super clean. We love it here and look forward to booking again for next year! It is a nice and familiar place for us.
Guest favorite
Apartment in Marathon
4.97 out of 5 average rating, 105 reviews

Beachfront Condo w/ Ocean Views in Marathon

AnneRating, 5 stars1 month ago
This was our first family trip to the Keys and this location in Marathon was ideal! The condo was welcoming, beautiful and spacious for our family of 3. The balcony was our favorite place, which overlooked the pool and the seashore. The beach was lovely for shorter walks and just "being" with the ocean. Fun seashells & hermit crabs at low tide! Lots to do in the area -- definitely hoping to return next year. Mike was fantastic host & super helpful with questions.

Waterfront house rentals

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 favorite
Home in Cudjoe Key
5 out of 5 average rating, 6 reviews

Moana Hale Paradise #164 - Venture Out, Cudjoe Key

anthonyRating, 5 stars3 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.
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 favorite
Home in Marathon
4.91 out of 5 average rating, 179 reviews

Beachfront Villa - Florida Keys

MorganRating, 5 stars1 month 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
Home in Marathon
4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

AmandaRating, 5 stars3 weeks ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.
Superhost
Home in Cudjoe Key
5 out of 5 average rating, 4 reviews

Keysgetaway Retreat. Fish#Fun#Relax

DorindaRating, 5 stars27 months ago
It was a great place. She was on top of things. Water went out not just at her place the whole keys because of main break. She was on top of it went we let her know of the problem and she found out the problem and got back to us.
Guest favorite
Home in Marathon
4.97 out of 5 average rating, 115 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

SusanneRating, 5 stars1 day ago
The house was beautiful!We thoroughly enjoyed all the outdoor spaces.With 4 bedrooms and an 8 month old, the house offered many spaces for everyone to be comfortable. The beds were comfortable and we were all well rested. The rooftop area for grilling and chilling was amazing. The outdoor seating area off the main level was where we celebrated Father’s Day dinner. Morning snuggles were spent in the seating area off the den.The pool area was where we laughed and swam and had many a cocktail. We loved our week as a family there and had no reason to leave except for a few dinners out.Andy was very responsive, dropped off bagels one morning and a great resource for recommendations. Highly recommend Anglers Terrace as we loved our week there!
Guest favorite
Home in Key Colony Beach
4.95 out of 5 average rating, 20 reviews

Private Pool! Luxury Paradise Pointe, Pet Friendly

KimberlyRating, 5 stars1 month ago
Amazing Stay in the Florida Keys! We had an absolutely incredible time at this home in the Florida Keys! Everything about our stay was perfect. The house was clean, comfortable, and had everything we needed for a relaxing getaway. The highlight was definitely the pool — it was beautiful, well-maintained, and the perfect spot to unwind after a day of exploring. The outdoor space was peaceful and made it feel like our own private paradise. Loved the tv out by the pool! We couldn’t have asked for a better place to stay. The location was great, the home was even better than expected, and we left feeling completely refreshed. Highly recommend and would definitely stay here again!

Waterfront condo rentals

Guest favorite
Condo in Key West
4.96 out of 5 average rating, 75 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 favorite
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 favorite
Condo in Duck Key
5 out of 5 average rating, 38 reviews

Oceanfront and Sunrise Views!

StephenRating, 5 stars4 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 stars1 week 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!
Guest favorite
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.
Guest favorite
Condo in Key West
4.9 out of 5 average rating, 211 reviews

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

AlexRating, 5 stars1 week ago
Jennifer’s place was exactly what we were looking for, it was a quiet corner unit with lots of space for four guests, a large kitchen (we love to cook elaborate meals even when we travel and we had everything we needed here), great views of the harbor, was squeaky clean, and ample parking. Jennifer communicated everything we needed to know well ahead of time and promptly replied to any questions we had. Would absolutely stay here again!
Top guest favorite
Condo in Marathon
4.96 out of 5 average rating, 104 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

PaulRating, 5 stars2 weeks ago
Host was extremely helpful and communicative. Check in was a breeze and all the amenities needed for a pleasurable stay. Bonus outdoor bait freezer!
Guest favorite
Condo in Key West
5 out of 5 average rating, 12 reviews

Sundown Refuge by AvantStay | Week-Long Stays

HollyRating, 5 stars1 month ago
The location couldn't be better. Large deck with view of the ocean in distance, very nice large pool just steps away, very quiet (except occasional airplanes - well, it's a small island after all) and the 5:00 pm fog horn last-boarding-warning from the cruise ship in port... kind of appropriate since the building's architecture looks a bit like a cruise ship - added to the vibe. Oh the SUNSET VIEW!! Within walking distance to the best part of Duval, the best restaurants and less than 15 minute bike ride to the best (Ft Zachary) beach. We Will be back if we can!!

Quick stats about waterfront rentals in Summerland Key

  • Total rentals

    160 properties

  • Nightly prices starting at

    R723 ZAR 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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