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Vacation rentals with a kayak in Estero Island

Find and book unique kayak rentals on Airbnb

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Popular amenities for Estero Island kayak rentals

House rentals with a kayak

Guest favorite
Home in Cape Coral
5 out of 5 average rating, 38 reviews

OceanLux_GulfAccess+Pool+Kayak+Bikes+Fishing+Games

KrystinaRating, 5 stars2 weeks ago
Olya’s home is wonderful. It was very clean, well decorated, and smelled great. It’s centrally located and in close distance to many of the beautiful Florida beaches. The home was full of everything we needed for our stay. The family had a blast kayaking the canal, fishing and swimming in the pool. It had plenty of room for all 8 of us. We enjoyed our family vacation and would love to stay at Olya’s again in the future!
Guest favorite
Home in Cape Coral
4.92 out of 5 average rating, 59 reviews

DownTown Villa WaterFront/Kayaking/Heated Pool

MakennaRating, 5 stars3 weeks ago
Host was super nice, and he accommodated an early check in for our group! He responded fast and with clear messages. The house itself was beautiful and looked exactly like the pictures! Will definitely stay here again!
Top guest favorite
Home in Cape Coral
4.97 out of 5 average rating, 33 reviews

Chasing Sunsets SLT wtr pool, kayak, paddle & fish

KellyRating, 5 stars1 week ago
Mindy was amazing and extremely helpful- quick to respond to messages and she provided her phone number so that we could call about anything. We had a wonderful visit at this beautiful home sitting on the canal. This home is close to all of the beaches that we wanted to explore - within a 25 to 30 minute drive - which wasn’t bad for us. The pool was so magical overlooking the canal with spectacular sunsets! Early morning coffee on the dock was just what the doctor ordered for a peaceful start to each day. Bikes were such an extra perk. I was able to ride down to the country club every evening (it is open to the public) and enjoy evening concerts outside when they had them. Perfect for little tots. Very accommodating regarding high chairs and crib. Overall our family had a magnificent time and made memories to last a lifetime! Thank you ‘Mindy! 😊
Top guest favorite
Home in Cape Coral
5 out of 5 average rating, 27 reviews

Escape To Your Personal Lakefront Villa On 8 Lakes

LisetRating, 5 stars1 month ago
What a great place to stay!!! We had an amazing weekend!!! Richard was very kind and communicative from start to finish. The house has a very good vibe. It is in very neat condition and spotless (tidy, clean, and very well organized). The patio/lanai is the best place for a morning coffee. We also loved the kitchen window overlooking the pool, practical for keeping an eye on kids and the sunlight is amazing. We also felt very safe and comfortable. The setting was incredibly tranquil, perfect for a relaxing getaway. Excellent amenities, comfy beds, quite and peaceful. Our experience was nothing short of amazing. We will definitely come back very soon since we love the city of Cape Coral, and this is the best place to stay. Thank you for such a memorable stay—we will definitely be back!!!
Top guest favorite
Home in Cape Coral
5 out of 5 average rating, 28 reviews

Cape Coral home with a large heated pool

StefanieRating, 5 stars3 days ago
We had a fantastic stay at this property. The location is perfect – quiet, yet close to everything you need. The house was very clean, well-equipped, and had everything we could possibly want. We especially enjoyed the pool and made great use of the kayaks. A big highlight was being able to dock our rented boat right at the house on the canal. There’s also a lovely bar just around the corner with live music on the weekends. We were a group of four and had plenty of space. Everything was very comfortable, and we felt right at home from the moment we arrived. We would definitely book this place again – highly recommended!
Superhost
Home in Cape Coral
5 out of 5 average rating, 4 reviews

The Tarpon Bay - Cape Coral

AleshiaRating, 5 stars2 months ago
Our stay at the Tarpon House was nothing short of incredible. The home is gorgeous and looks brand new. Everything we needed was provided from dish soap to beach chairs. The pool was our favorite part! Gorgeous sunset dinners at the Tiki Hut. Could not have asked for a better vacation home. The host were amazing and had it all ready for us upon arrival. We will definitely be back!
Guest favorite
Home in Cape Coral
5 out of 5 average rating, 40 reviews

Coastal Therapy -Gulf Access w/ Pool, Dog Friendly

BridgetRating, 5 stars4 days ago
Absolutely beautiful home with updated fixtures and amenities. We loved the location right on the water with access to kayaks and the pool was incredible for our family. We loved checking out the different beaches, islands and restaurants in the area. Highly recommend and we are so thankful for this home helping our family have the vaca of a lifetime! Host was incredibly responsive and home met and exceeded our expectations!
Guest favorite
Home in Captiva
4.95 out of 5 average rating, 37 reviews

Beachfront Island Retreat | 360 Views & Privacy!

JessicaRating, 5 stars1 month ago
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!

Cottage rentals with a kayak

Top guest favorite
Cottage in Bonita Springs
4.98 out of 5 average rating, 60 reviews

The Enchanted Cottage on the Imperial River

BeaRating, 5 stars2 weeks ago
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!
Superhost
Cottage in North Fort Myers
4.77 out of 5 average rating, 13 reviews

Last Minute-Villa Seafan-modern, pool, kayaks

LeAnneRating, 5 stars2 months ago
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.
Superhost
Cottage in Cape Coral
4.63 out of 5 average rating, 49 reviews

Villa The Island Hideaway 2

MartineRating, 5 stars4 months ago
SĂ©jour trĂšs agrĂ©able, calme une vrai vacance, belle maison propre, piscine et spa, et la maison Ă©tait Ă©quipĂ© de tout, rien ne manque. De trĂšs belles chambres avec des lits trĂšs confortables. La cour arriĂšre donne sur un petit canal, de toute beautĂ© de voir les bateaux passer, les gens nous salut. TrĂšs agrĂ©able. Tout est Ă  proximitĂ©, Ă©picerie, magasin, resto, la marina TARPON POINT Ă  voir wow de wow tant la vue avec les bateaux que les restos succulent et les boutiques. A tout les samedis matin, Ă  environ 10 minutes de la maison il y a un marchĂ© en pleine air, le Market Farm, super bien, et aprĂšs Ă  cĂŽtĂ© il y a le restaurant le Rusty’s pour le dĂźner belle terrasse. Et tout c’est endroit avec la possibilitĂ© d’amener votre chien. L’hĂŽte Ingrid est trĂšs gentille, comique, et rĂ©pond trĂšs rapidement Ă  vos questions. C’est une maison Ă  rĂ©server. J’y retournerais certainement. Merci Ingrid de ta gentillesse. Xx
Top guest favorite
Cottage in Naples
4.9 out of 5 average rating, 249 reviews

Cottage Close to Vanderbilt Beach Heated Pool

LuisRating, 5 stars1 week ago
The home was amazing with a heated pool, 5 minute drive and 20 minute walk to vanderbilt beach. The kitchen has everything you need and the bedrooms were great.
Cottage in Saint James City
5 out of 5 average rating, 7 reviews

Flamingo Bay Cottage

GregoryRating, 5 stars5 months ago
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!
Cottage in Matlacha
4.88 out of 5 average rating, 42 reviews

The Coqui Palace

LaurenRating, 5 stars4 months ago
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!!
Guest favorite
Cottage in Bonita Springs
5 out of 5 average rating, 17 reviews

Quiet Riverside Cottage in Downtown Bonita Springs

SinaRating, 5 stars5 months ago
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 !!
Cottage in Bokeelia
4.75 out of 5 average rating, 174 reviews

Captains Cottage

George Rating, 5 stars3 weeks ago
Very nice cottage was perfect for weekend getaway

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Lee County
  5. Fort Myers Beach
  6. Estero Island
  7. Rentals with a kayak