Vacation rentals with a kayak in Summerland Key

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Popular amenities for Summerland Key kayak rentals

House rentals with a kayak

Guest favorite
Four kayaks are neatly stacked against a white fence, with green turf laid beneath them. Nearby, a boat lift is visible along the water, framed by tropical palm trees under a clear blue sky.
Home in Marathon
4.95 out of 5 average rating, 131 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

JenniferRating, 5 stars6 days ago
Although the place wasn’t ready when we arrived, Ryan was a great communicator! He addressed every issue we had (which were NOT within his control) and responded in a timely manner. He offered a fair solution and allowed us to sit back, relax and enjoy paradise! I’d highly recommend and hope to be back sometime soon!
Superhost
A spacious deck is featured with several comfortable seating options overlooking tranquil waters. Lush greenery lines the opposite shore, providing a serene backdrop. Bright skies create an inviting atmosphere, highlighting the direct waterfront access and outdoor living potential.
Home in Marathon
4.8 out of 5 average rating, 35 reviews

Luxury Waterfront Retreat with Dockage & Pool

SharonRating, 5 stars2 weeks ago
We enjoyed our stay. The home was comfortable and very clean. It was nice to have a view of the water and a heated pool! The rooms were comfortable and accommodating for our family. Naomi was quick to respond when we had questions. I would stay here again! This spot was close to many restaurants, grocery stores, and right on bike paths!
Superhost
A spacious living area features comfortable seating arrangements with two leather sofas facing a decorative area rug. The open-concept design connects to a dining space and a fully equipped kitchen, all accented by natural light from multiple windows.
Home in Marathon
5 out of 5 average rating, 3 reviews

Waterfront Oasis3/2 Direct Ocean

JohnRating, 5 stars9 months ago
Beautiful views and great spaces! We’ve stayed in Marathon several times in different canal houses with our family of 7, and this property is now our new favorite. We couldn’t get enough of all the beautiful views from sunrise to sunset whether it was on the porch, in the pool, or out by the Tiki Hut. Every bedroom has water views as well. Boat access was an easy out to snorkeling, diving, fishing, or whatever you like to do. There are two kayaks for use, which made for some nice outings to explore the immediate area. The kitchen had everything needed for cooking, and even had an extra under-the-counter ice machine. We had a great time here, and would stay again. Thank you to the owners for sharing your property.
Superhost
A wooden deck extends over the water, featuring two lounge chairs oriented towards the ocean. A barbecue grill is positioned nearby, with lush greenery framing the scene. The clear blue water and bright sky create a serene backdrop.
Home in Marathon
4.86 out of 5 average rating, 7 reviews

Dolfan Oceanfront Cottage Direct oceanfront with 5

ShawnRating, 5 stars15 months ago
This place was great. We close our business down every year for a week so staff can get away and every year some join us for a getaway. This year we came here, the Dolfan house was awesome. The view was amazing and having a boat dock to park the rental boat made it all the better. Idaho’s # 1 steakhouse (Wolf Lodge Steakhouse) will be back next year. Thank You
Superhost
A comfortable living area is showcased with a dark leather sofa and a rustic coffee table set on a patterned rug. Large windows offer views of the canal, while modern decor and a ceiling fan enhance the inviting atmosphere.
Home in Cudjoe Key
4.8 out of 5 average rating, 20 reviews

Keys Time #437 - Cudjoe Key, Oceanfront Community

TerriRating, 5 stars3 months ago
Jean was wonderful! She was very attentive and made sure that our stay was most enjoyable. Our rental was clean and comfortable. The kitchen was fully equipped. The location is great.
Guest favorite
A dining area features a glass-top table surrounded by four woven chairs. Light flows in from nearby doors, illuminating the open layout that connects to a welcoming living space. Wall-mounted decor and book shelves add another layer of character.
Home in Marathon
4.94 out of 5 average rating, 32 reviews

Waterfront w/pool and hot tub

ErinRating, 5 stars3 weeks ago
We had a great time at this location. They had everything we needed and Key Colony is a perfect spot to vacation.
Guest favorite
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviews

Oceanside home 107,dock,kayaks,bikes,pool,fishing,

JessicaRating, 5 stars3 weeks ago
If you are looking for a relaxing and peaceful location, this is the place! John was so helpful! The place was exactly as described. Our family felt right at home and enjoyed being away from the busyness of larger keys! Close to Key West and some amazing restaurants!
Guest favorite
An open living area is highlighted by wooden ceilings and light-colored walls. A spacious sectional sofa with decorative pillows is positioned near a television. An inviting coffee table sits in front, with a dining area visible to the side, featuring a set of elegant white chairs and a wooden table.
Home in Key Colony Beach
4.87 out of 5 average rating, 15 reviews

Fun in the Sun!

BrentRating, 5 stars1 month ago
Great attached townhome/duplex with privacy fence between the other side. Great private pool just on the canal! The bottom story was perfect for extended family to have privacy but still be close! We even saw a manatee in the canal.

Cottage rentals with a kayak

A bright living area features light-colored furnishings with nautical accents. Large windows offer views of the water, while a flat-screen TV is positioned on a stylish stand. The adjoining dining area showcases a white table with matching chairs surrounded by plants, enhancing the airy environment.
Cottage in Cudjoe Key
4.81 out of 5 average rating, 95 reviews

OCEANIA... water front cottage retreat ~

RachelRating, 5 stars7 months ago
If we could rate this 6+ stars out of 5, we would! Manuel was super easy to reach, he provided simple and clear instructions, the guards at the gate were easy to work with and available for 24/7 entry and check in.. the location is unbeatable for a boat owner! You dock right at your back door, clean your fish at the back door OR at the marina, immediate access to the Atlantic.. perfection. The home itself is extremely clean & beautiful. The kitchen and bathrooms were all stocked with anything you’d need as well as even the laundry room! We truly felt at home but twice as relaxed! Thanks Manuel!!
Superhost
A bright window offers views of the canal and vibrant outdoor scenery. Two stools are positioned in front of the window, inviting guests to relax and enjoy the surroundings. Colorful decorations add a charming touch to the space, enhancing the coastal atmosphere.
Cottage in Cudjoe Key
4.7 out of 5 average rating, 145 reviews

Calypso Cottage

CourtneyRating, 5 stars1 week ago
Place was exactly like described, super quaint and had a great homey cottage feel. Neighbors were all super friendly as well. We really enjoyed being able to sit outside on the canal and enjoy our breakfast/dinner as well as playing any games. Would highly recommend this place, not far from key west a matter of 35-45 min depending on traffic
The private saltwater pool is framed by tropical plants and bright blue sky. Lounge chairs are positioned nearby, alongside decorative elements and pots. The serene atmosphere offers a refreshing retreat, inviting relaxation and enjoyment in the beautiful surroundings.
Cottage in Key Colony Beach
5 out of 5 average rating, 10 reviews

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach

DawnRating, 5 stars12 months ago
Leeann’s place exceeded our expectations! She was incredibly responsive to any concerns or inquiries we had throughout our stay. The added perk of access to Glunz Beach Resort with its beach, pool, and gym made our experience even more delightful. The house was equipped with everything we needed for a comfortable stay. Thank you, Leeann!
Superhost
A coastal view features multiple white houses with balconies situated along the waterfront. Palm trees sway gently in the breeze, and clear blue skies create a serene backdrop. Vehicles are parked in the driveways, emphasizing accessibility to the beachfront.
Cottage in Cudjoe Key
New place to stay

Ocean Breeze at Venture Out 537

Quick stats about vacation rentals with a kayak in Summerland Key

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ588 before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Destinations to explore