Holiday rentals with a kayak in Monroe County

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Popular amenities for Monroe County kayak rentals

Holiday House Rentals with a Kayak

Top Guest favourite
Home in Key Colony Beach
4.98 out of 5 average rating, 124 reviews

Paradise found!Key Colony Beach,Cabana Club.

ColinRating, 5 stars2 weeks ago
We had a great week at Kari's place. We were blown away by the view from the terrace. The apartment was well appointed and had everything we needed. The use of the nearby Cabana club was a real bonus. Colony Key is about an hour from Key West, so it was well located for all sorts of activities. Would love to return one day. Thanks Kari. Colin & Lynne Moore. Buckinghamshire, UK
Superhost
Home in Key Largo
4.91 out of 5 average rating, 151 reviews

Tiny Home on Waterfront | Bay Views | Deck | Pool

VikranthRating, 5 stars3 weeks ago
Great great getaway place to relax. Right on the waterfront. You can get your boat, Jet ski and enjoy your stay. I loved watching sunrise with my cup of coffee.
Guest favourite
Home in Miami
4.94 out of 5 average rating, 34 reviews

Lake Home Fishing Game 360 Infinity Heat Pool L46

DiamondRating, 5 stars6 days ago
The house was perfect. We’ll most definitely book it again. The host was great with responding and communicating. The house was well equipped it had everything we needed we barely left and didn’t want to go back home. The house was immaculate I love the white marble floors and the smart kitchen. We enjoyed our stay I can’t wait to return.
Top Guest favourite
Home in Marathon
4.98 out of 5 average rating, 47 reviews

Flamingo Palms-Summer discounts-NOW available

LaurenceRating, 5 stars2 months ago
Excellent host and great home and location. Fishing from the dock, grill on the patio. Lovely decor throughout the property. Made for an excellent choice for my wife’s milestone birthday celebration and Ramon and Ana made that extra special with a birthday banner. Would visit again travel plans permitting
Guest favourite
Home in Marathon
5 out of 5 average rating, 23 reviews

Spacious lux home, private pool/spa, 80' dock

KelliRating, 5 stars3 weeks ago
Beautiful, roomy, comfortable, well appointed home. Has absolutely everything you could need for an incredible vacation! Great little gym, really nice bikes, coolers, pool floats, beach umbrellas, kayaks and paddle boards. The entire game room area is such a great place to hang out. Good size pool, shade keeps it nice and cool. Quiet neighborhood. Owners are super responsive, very helpful. We really loved this place!
Guest favourite
Home in Key Largo
4.91 out of 5 average rating, 107 reviews

Sunsets In Palms Paradise

TaylorRating, 5 stars1 month ago
We thoroughly enjoyed this house! The backyard is amazing with plenty of space to play cornhole, throw frisbees, and enjoy the beautiful weather. We saw a manatee behind the property and with the provided paddleboard got to see it close up as well! The house was clean and had all desired amenities . We will definitely be back.
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 77 reviews

New Private 4/3 Single Family - Kayaks & Bicycles+

BeckyRating, 5 stars4 days ago
We had a wonderful week at Blue Treasure. I highly recommend this rental, especially for families. All the listed amenities were in excellent shape and available for our use. We enjoyed bike riding, kayaking, fishing, grilling, and the outdoor games. The yard and pool were pristine and a welcome place to relax after a day exploring Marathon and the surrounding area.
Guest favourite
Home in Key Largo
4.92 out of 5 average rating, 53 reviews

Treetops

LilyRating, 5 stars3 months ago
This place was such a nice experience. The views were gorgeous and the area was peaceful. It was really a bargain for the price. I highly recommend it!

Cottages with a kayak

Guest favourite
Cottage in Islamorada
4.97 out of 5 average rating, 87 reviews

Islamorada bungalow 2 bed & pool

AmandaRating, 5 stars2 weeks ago
The hosts were very responsive and accommodating to our needs. The pool was great and the place was pristine!
Superhost
Cottage in Cudjoe Key
4.83 out of 5 average rating, 6 reviews

Ocean Breeze at Venture Out 537

ChristopherRating, 5 stars3 weeks ago
We are first timers to the keys and were not only on our honeymoon, but also our first vacation away alone for a week. We could not have been happier. We loved every minute of our stay both on the property and in the entire area. John communicated everything clearly from the booking and we had no reasons to contact him.
Top Guest favourite
Cottage in Marathon
4.97 out of 5 average rating, 36 reviews

Catch n' Relax Canalfront Cottage in Marathon

StefaniRating, 5 stars2 weeks ago
We have three boys and they LOVED being able to fish anytime they wanted. We caught over 12 species of fish from the back dock. The kayaks were very handy! We just rented two more and We loved getting out in the mornings for a family kayaking adventure and the boys fished any chance they got. They even caught a nurse shark! The house was clean and well decorated. There were handy items such as sunscreen and life vests. It was a great place for a family of five.
Cottage in Islamorada
4.75 out of 5 average rating, 175 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

JaceyRating, 5 stars4 months ago
We loved staying here for the two nights we were on the Keys. The patio outside was great for looking at the stars or sipping coffee and watching manatees. We would definitely return!
Guest favourite
Cottage in Cudjoe Key
4.93 out of 5 average rating, 130 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

AllieRating, 5 stars2 weeks ago
Ellen was an absolutely amazing host! When we arrived, there was a small hiccup, but Ellen responded immediately. She got it taken care of instantly hand her husband even called us personally to apologize, which meant a lot — truly top-notch customer service. Aside from that small hiccup, the place was fantastic! It had everything we needed for a relaxing stay, from great amenities to a peaceful atmosphere. We felt right at home and really enjoyed our time there. We would absolutely stay again. Thank you, Ellen, for being so responsive, kind, and professional!
Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviews

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

MatthewRating, 5 stars2 months ago
What a fantastic place to stay in Marathon! LeeAnn really makes sure you feel right at home. Forgot a toothbrush? Didn't pack or want to buy shampoo? No problem, it's there! The pool is amazing, house is spotless, and the Key Colony Beach community is the best. It is quiet and relaxing while also being in the heart of everything to do in the Florida Keys. LeeAnn is so nice and responsive, she got back to us quickly with any questions that we had. Overall, this was one of the nicest places that my family and I have ever stayed on a vacation. 10/10 would recommend to anyone!
Cottage in Cudjoe Key
4.81 out of 5 average rating, 99 reviews

OCEANIA... water front cottage retreat ~

DeniseRating, 5 stars1 month ago
Place was great. We loved the kayaks and Bikes that were there. Very clean and spacious. Beautiful view being on the canal. my negative I would say, which has nothing to do with the host, We were aware of the $125 resort fee, And our fee was increased to $145 cause my son’s large pickup. Curious as to what that fee actually pays for. We would definitely stay again.
Guest favourite
Cottage in Key Largo
4.91 out of 5 average rating, 86 reviews

THE PARADISE

JessicaRating, 5 stars1 week ago
We were there because we was celebrating my husband‘s birthday and our wedding anniversary . It was a great place to stay highly recommend it. Quiet and comfortable atmosphere for a great long weekend. Luis Alberto and his wife very attentive. It makes us feel like we’re around family.. can’t wait to come back again. Our favorite place to go for now on.

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