Vacation rentals with a kayak in Estero Island

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Top-rated kayak rentals in Estero Island

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Guest favorite

Guest suite in Saint James City

4.98 out of 5 average rating, 95 reviews

Waterfront island private suite with private pool

Take it easy at this Island, PRIVATE, waterfront getaway! Enjoy a large PRIVATE electric heated pool, located directly on the water. Kayak dock and KAYAKS free with rental. Completely private entrance. Please be aware that Pine Island is a somewhat remote island without many commercial businesses and no public beaches but there’s more than plenty to do! 5 restaurants within 1 mile by car and many more within 8 miles. Located on a quiet residential street, directly on the water. Car is a must!

Guest favorite

Home in Cape Coral

4.99 out of 5 average rating, 196 reviews

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

Guest favorite

Cottage in Saint James City

5 out of 5 average rating, 38 reviews

Waterside Cottage

Enjoy our peaceful little island paradise nestled beneath sprawling oaks and scattered palms just minutes from St James City’s restaurants and bars. Just under 1/2 acre is yours to enjoy. Watch the manatees and dolphins swimming in the canal while you grill your catch of the day, or your fresh pick of the day from St James Fish House just down the street! Inside enjoy a fresh new contemporary and stylish cottage with everything you will need to make your stay comfortable, enjoyable and fun!

Guest favorite

Guesthouse in Cape Coral

4.94 out of 5 average rating, 116 reviews

Pool Modern Apartment

Location! Location! This apartment is close distance to Deli, restaurants and supermarket . The house faces the canal with breathtaking views we have cameras facing the canal and pool area in order to protect guests from any small animals that might be around. The apartment is attached to the main house with one bedroom one bathroom living room and a functional full kitchen in the Lanai area Is only for 2 persons. No children allowed. After May 2025 pool will be shared by 1 or 2 more guest.

Guest favorite

Home in Naples

4.98 out of 5 average rating, 160 reviews

Gulf Access Sanctuary, Kayaks, Bikes, ebikes

A renovated mid century modern house with natural peaceful views out of every window and slider. No detail spared, as it was going to be our forever home. Located on an ocean access canal, extremely safe, quaint and friendly neighborhood, just off 41. The backyard has a large shaded sitting area with a gas grill and fire pit. The dock hangs over the water with seating and swim ladder. 2 tandem kayaks, fishing rods & tackle, adult & children’s bicycles, beach chairs, and so much more.

Guest favorite

Home in Captiva

4.92 out of 5 average rating, 106 reviews

Blue Laguna - Vacation in paradise!

Beautiful and welcoming are just two words to describe this magnificent, 4 story home with heated private pool and sweeping 360 degree water views from the observation deck. Blue Laguna features 3 bedrooms and 3 full baths allowing this home to sleep up to 6 people. Two screened in lanai's so you can sit and enjoy the island breeze and leave the sliding doors open for a true island nature experience during the colder seasons. A golf cart for 4 persons is also included in the rental.

Guest favorite

Home in Captiva

4.95 out of 5 average rating, 110 reviews

Steps To Private Beach Captiva Retreat Golfcart

Relax and Reconnect at Our Charming North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly (with applicable fees), it’s easily accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach start making memories.

Guest favorite

Guest suite in Matlacha Isles-Matlacha Shores

4.84 out of 5 average rating, 331 reviews

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

Guest favorite

Home in Naples

4.99 out of 5 average rating, 118 reviews

Pool Bikes & Beach | Paddle Board Included

We welcome your family of up to 2 adults & 3 children. You will be close to sandy beaches, great restaurants and shopping at this great North Naples Location. Just a few minutes from Vanderbilt Beach and Wiggins Pass Park. You will love all the great amenities and be able to relax in this brand new clean apartment. Amenities, Bikes, paddle board, beach wagon and beach towels. Very easy to check-in, you will have your own private entrance and private one car parking available.

Guest favorite

Home in Matlacha

4.98 out of 5 average rating, 189 reviews

Matlacha Paradise! NEW Waterfront Home-Free Kayak

Matlacha is for LOVERS! Lovers of relaxation, fishing, art, friends, social scenes and enjoying Life in a beautiful location ON THE WATER! Matlacha had damage from Ian. Our new home - none. You can still walk to great restaurants, shops and the fishing bridge. Enjoy the water in Matlacha & the Barrier Islands. Use our 1 person kayak for fun or fishing from our 8'X22' FUN & SUN deck docked in the back canal with picnic table & loungers. Relax, sun, grill and fish.

Guest favorite

Home in Fort Myers

4.94 out of 5 average rating, 115 reviews

Cottage between Sanibel and Edison / Ford Estate

This is the ultimate getaway for our guests. Yes…. you’re going to have an entire house for yourself . Feel free to enjoy 2 bedroom / 2 bathroom house with a Florida room, plus outside patio with gazebo(BBQ) and large back yard. Our newly renovated retreat is in the perfect location that is close to the beach, near all the best restaurants, and has all the amenities you will need for a breezy family vacation. Cleaning fee only $49!

Superhost

Home in Bonita Springs

4.85 out of 5 average rating, 172 reviews

Lovely Renovated Family Home in Heart of Bonita

*NEW AC UNIT put in June 2023* Inviting family home located near downtown Bonita Springs. This is a family friendly house with comforts and conveniences of home. Parking for 2 and large yard for outdoor play. 15 mins to Coconut Point Mall & Marimar Outlet, Prado Stadium movies, casino, shopping, mini golf, and fabulous restaurants, this house is the comfortable place with all the conveniences of home for a Florida family getaway!