Waterfront vacation rentals in Summerland Key

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Popular amenities for Summerland Key waterfront rentals

Waterfront apartment rentals

Top guest favorite
Apartment in Marathon
5 out of 5 average rating, 14 reviews

Oceanfront Getaway in Marathon!

TriciaRating, 5 stars2 months ago
Condo was great. Exactly as described. 2 minute walk to the large heated swimming pool and beautiful ocean view. Shuffle board and ping pong available to play near the pool area. Safe, quiet, gated condo community. Within short driving distance to many great restaurants and activities. Frank responded within hours and answered my questions. We would recommend this rental and would gladly stay here again!
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.
Guest favorite
Apartment in Key West
4.87 out of 5 average rating, 38 reviews

Key West Condo with Pool & Boat Slip Access

AtishRating, 5 stars1 week ago
Great place to stay with my family in Key West. everything was clean and as advertised. Having parking was a bonus everything is close by (driving) or a 15-30 minute walk.
Top guest favorite
Apartment in Marathon
5 out of 5 average rating, 20 reviews

#1 Island Hideaway 89 - OCEAN FRONT

SamanthaRating, 5 stars2 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 favorite
Apartment in Islamorada
4.98 out of 5 average rating, 66 reviews

Hidden Gem Islamorada | 1st Floor

MelodyRating, 5 stars2 weeks ago
We had a great stay in Islamorada at this house. Location is perfect! We were minutes away from so many things. My daughter loved looking for all the little lizards that scattered as we entered the patio. The house was well stocked with things we needed. Beach stuff wise, there are noodles and some camping chairs - no kids sand toys so plan to bring those if you have little ones. There were 4 beach towels provided. The washer was broken while we were there so hopefully it is repaired soon. Of note, the mattresses are very firm so if you like a softer mattress then it might not be the house for you. Also, if you happen to find a man’s ring in the house, it might be my husband’s. Please let the host know so we can arrange to get it back.
Guest favorite
Apartment in Key West
5 out of 5 average rating, 5 reviews

Henry's Penthouse On The Ocean

WilliamRating, 5 stars1 month ago
The Condo was spacious, beautiful, well furnished, very clean and the location was perfect. Henry was great to work with. We rented a golf cart and traveled almost everywhere in Key West by golf cart.
Superhost
Apartment in Marathon
4.86 out of 5 average rating, 51 reviews

Little Venice in Marathon (in the Beautiful Keys)

AlisonRating, 5 stars3 weeks 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!
Superhost
Apartment in Key West
4.86 out of 5 average rating, 98 reviews

Penthouse in Paradise

EllenRating, 5 stars3 weeks ago
Enjoyed our stay. The place was beautiful and matched the description. Just disappointed couldn’t use jacuzzi tub. Otherwise no isssues

Waterfront house rentals

Guest favorite
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!!!
Top guest favorite
Home in Marathon
4.99 out of 5 average rating, 137 reviews

Cancellation Deal: 08/02 thru 08/09

KevinRating, 5 stars1 week ago
The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie
Guest favorite
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
4.62 out of 5 average rating, 165 reviews

Ocean Front Home in Great Location

MichaelRating, 5 stars1 month ago
Fantastic place for a home base while the beautiful keys. Close enough to key west for an upbeat day, very quiet in the evening. If anything, I’d say I was expecting less from the description and was very surprised at how nice this place is. I would stay here again in a heartbeat!
Guest favorite
Home in Marathon
4.89 out of 5 average rating, 66 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

RobinRating, 5 stars2 weeks ago
This home is even more than the pictures show! It is an extraordinary home for people who love the sun, shade, beach, and the beautiful home just makes it a luxurious vacation. I could not find one aspect I didn’t love.❤️
Guest favorite
Home in Marathon
4.91 out of 5 average rating, 179 reviews

Beachfront Villa - Florida Keys

MorganRating, 5 stars4 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!
Superhost
Home in Cudjoe Key
4.89 out of 5 average rating, 19 reviews

Mermaid Magic at Venture Out

MistyRating, 5 stars3 months ago
Adorable little 2 bdrm home on a bay. Very cute, clean. Kids can fish at back of the house. Plenty of activities to do on the property. Feels like a 55 and up community, lots of older women walking in the pool that didn’t like kids playing. “Resort” fee $125 NOT included which is very overpriced, but does pay for security and the grounds are very safe. Supplies for laundry and kitchen well stocked.
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.

Waterfront condo rentals

Superhost
Condo in Duck Key
4.88 out of 5 average rating, 107 reviews

Villa 5027 on Duck Key BOAT SLIP available

AlexisRating, 5 stars1 month ago
The place was perfect. The patio views were amazing to just sit and watch the sunset. The marina across the street was very convenient to launch our boat from. Very peaceful location. Angler and ale restaurant across the street was delicious
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 stars2 months 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.
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.
Superhost
Condo in Key West
4.85 out of 5 average rating, 155 reviews

Anchor Drop modern elegance upgrades throughout vi

ElizabethRating, 5 stars1 month ago
Exceptional stay. Anchor Drop was a top Airbnb property in our book.,Would definitely look to return to both Key West and the property. Host was responsive, explicit, and helpful. Space was as described and very well appointed, clean, and comfortable. First time to Key West and was very satisfied with our accommodations, location, and area. Thank you!
Guest favorite
Condo in Key West
4.87 out of 5 average rating, 201 reviews

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

JustinRating, 5 stars4 weeks ago
We had a great stay at Jennifer’s condo! It was clean, well-appointed, and had beautiful views of the harbor. The location was perfect—just a short drive to all that Key West has to offer. Jennifer was a proactive host and kept us well informed throughout our stay. Highly recommend!
Top guest favorite
Condo in Marathon
4.96 out of 5 average rating, 102 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

AlexRating, 5 stars2 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.
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!!
Top guest favorite
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

    G$8,365 GYD 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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