
Holiday rentals with a kayak in Naples
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Top-rated Accommodation with a Kayak in Naples
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Holiday House Rentals with a Kayak

Flirty Flamingo Gulf Access Cape Coral Home
We had a great stay in Amanda's house. There was everything you need. What we enjoyed most was the pool and the unique view from the terrace. We definitely recommend this accomodation to those who want to spend some relaxing days in Cape Coral!

5 Star Paradise Plus/Canal/Pool/Spa/Kayaks
This is the second time my family has stayed at Connie & Dale’s. We absolutely love it. The home is gorgeous and well equipped with everything you need. The outdoor patio area and pool/ jacuzzi is amazing. So beautiful and relaxing. Will definitely be back !

Waterfront, Gulf Access, Dock, Heated Pool & Kayak
We had an amazing stay! The place was immaculately clean—honestly one of the cleanest Airbnbs we’ve ever stayed in. Everything was spotless and so well cared for, which made it feel extra comfortable and relaxing. It is well equipped with everything needed for a stay away from home. The highlight for us was the beautiful pool area and the stunning canal water views—such a peaceful setting, especially in the mornings and evenings. The area is safe and nice for morning and evening runs or walks as well. Merrill was super responsive and made everything easy from start to finish including voluntarily offering a late checkout to accomodate our flight schedule! We would definitely love to come back and highly recommend this lovely island retreat to anyone looking for a clean, scenic, and relaxing getaway! Ariani’s is the little Italian restaurant recommended in the hosts guidebook. Make sure to plan on dining there during your stay! Great choice!

Waterfront Pool Home w/Outdoor Oasis/King Beds
5 star review from Ohio! We loved Lorraine’s home! Besides the big things we were looking for, pool for the kids, canal for fishing, Lorraine made her home so inviting and comfortable for our stay! The home was clean, style and decor is beautiful, comfortable bedding, TV’s in every room, best shower I’ve ever had! We will most definetly recommend to others and would love to come back! Thank you!

Cheerful 3 bedroom home with heated pool!
We felt right at home in this rental. The kids loved the pool, the outdoor space was comfortable and quiet. Easy drive to anything you need and John was super responsive.

Coastal Therapy -Gulf Access w/ Pool, Dog Friendly
Overall we are beyond pleased with our stay. Coming from Ohio, we felt right at home with the fishing poles and kayaks. The location of the hole is right on a busy road and almost a corner lot, at night it got super loud with the street racers. From the previous guests they left cigarette butts in the pool area, which cleaning missed. We ran out of trash bags and paper towels and Jason was quick to respond and help out. We brought our two dogs, and they loved the patio and the dock just to bask in the sun. The beds were comfortable and the kids loved to play pool. Would highly recommend staying here and would stay again. Thank you Jason, and family for an amazing and memorable trip!

Beachfront Island Retreat | 360 Views & Privacy!
If you are looking for a Maldives trip in Florida, then book here! We had a flight delay and missed our ferry and Joe was proactive helping us book a captain to transport us to the home after hours. Not only is the place EXACTLY like the pictures you could not find more serene surroundings to drink your morning coffee and watch gorgeous sunsets on the deck with your family. Cooking at the house takes so much pressure with traveling with the toddler even though we booked Bo the private chef for the evening. Loved driving around the golf cart and now our almost two year old’s new word she learned, turtle after one she saw exploring. We saw dolphins as captain chris drove us back to the dock to go home, the worst part was having to GO HOME! 10/10 recommend. Book with Joe!

Gulf Access | Heated Pool | Family Friendly |
This property is really amazing and Brianna was an excellent host, on top of everything we needed for our stay.
Cottages with a kayak

The Enchanted Cottage on the Imperial River
We had an amazing week at Mona’s Enchanted Cottage! Enchanted we were! Mona is so friendly and communicative, offering tons of great local recommendations. The cottage is cozy, clean, private, and had everything we needed. We loved kayaking—fed turtles, saw manatees swim by, birds, and even an owl! A few small gators kept their distance but not curious enough to bother. Fishing from the dock was fantastic—I caught 25+ fish across 5 different species. There’s definitely more than you can count though. The bait shop with the funny name further down the road had the best bait and tips. The hot tub spa is the super nice kind. We grilled dinner most nights and had no issues with the internet to stream shows when it rained. The town is small and cute. You can definitely find a place to listen to live music every night. Our dog adored the doggy beach, and Barefoot Beach was super close with easy parking at 10 AM. We didn’t want to leave, 10/10—already planning to come back!

Last Minute-Villa Seafan-modern, pool, kayaks
This is a beautiful home. Well appointed and well maintained. Everything was spotless. I would stay here again in a heartbeat!! The host thought of almost everything. Kayaks, bicycles, pool towels, etc. My only recommendations for improvement would be facial tissues and fans for sleeping. That’s it! That’s all I could think of.

Villa The Island Hideaway 2
Wow! We loved this house. Great outdoor seating, loved watching the boats come and go. Pool and hot tub were fantastic. Great flat grill for dinners at home. Good restaurant options in the area. Cape Coral is close to so much, but away from traffic. Loads of windows and natural light. Very clean. Highly recommend.

Flamingo Bay Cottage
RedAwning was the perfect accommodation for our 3-day fishing trip. We docked the boat directly behind the house, which was equipped with a fish-cleaning station and comfortable outdoor patio. The hosts were friendly and responsive, even offering to replace the coffee maker we were having some trouble with. The house was clean and comfortable, and the kitchen well-equipped (including complimentary wine and water bottles!). It would have been nice to have a second bathroom, but otherwise it was perfect!

The Coqui Palace
Ernest was great! He was super responsive when we were trying to get the heat to work and was very proactive. He had renovated the place nicely after the area had experienced hurricane damage. The town is still in recovery but the neighbors were friendly when we were walking around. I will note that the current pictures (as of Jan 2025) are not up to date due to the renovations post hurricanes but all of the appliances/repairs are new and clean. and should not pose an issue on booking/staying at this house (i.e. the tiles in the bathroom are now white). We would stay here again!!

Quiet Riverside Cottage in Downtown Bonita Springs
Cute cottage! It was clean, comfortable, and a great location! Bradley was an amazing host! He had everything you could possibly need, and went above and beyond to make our stay perfect. Highly recommended !!

Cape Lake House Lake Front
We had two families and we both enjoyed our stay! The house was very accommodating for both our families with kids. We all enjoyed the salt water pool and patio. The information binder provided gave clear instructions for our stay and provided many recommendations for restaurants and activities to do. Stu and Cathy were very helpful and even personally check on us during our stay!

Captains Cottage
Very nice cottage was perfect for weekend getaway
Quick stats about holiday rentals with a kayak in Naples
Total rentals
50 properties
Nightly prices starting at
$186 AUD before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
30 properties have a pool
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- Naples Beach
- Captiva Island
- Lovers Key Beach
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- Barefoot beach Bonita Springs,FL
- Tigertail Beach
- The Club at The Strand
- Worthington Country Club
- Seagate Beach Club
- Delnor-Wiggins Pass State Park
- Heritage Bay Golf & Country Club
- Panther Run Golf Club
- Bonita National Golf & Country Club
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