Vacation rentals with a kayak in Naples

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Top-rated accommodations with a kayak in Naples

Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Cape Coral

4.99 out of 5 average rating, 174 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!

Oct. 17 – 24

$798 CAD per night

Guest favourite

Home in Naples

4.99 out of 5 average rating, 148 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.

Mar. 27 – Apr. 3

$666 CAD per night

Guest favourite

Guest suite in Matlacha Isles-Matlacha Shores

4.84 out of 5 average rating, 315 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!

Nov. 20 – 27

$146 CAD per night

Guest favourite

Home in Naples

4.94 out of 5 average rating, 104 reviews

Tropical Cottage by the Sea

Welcome to your own private home on private lot! This 1 bedroom/1 bath cottage comes with a million dollar view & is perfectly located in the beautiful Bayshore Arts District in Naples. Quiet neighborhood but close to beaches & lots of fun things to do! Beautiful wild life and tropical plants abound. Fish and kayak right in the back yard. Relax on the back porch where there's always a breeze! Bike over to the Botanical Gardens or one of the many restaurants close by! This is the one!

May 21 – 28

$319 CAD per night

Guest favourite

Cottage in Naples

4.89 out of 5 average rating, 225 reviews

House w/Heated pool close to Vanderbilt beach

*Road construction* ask before booking. Completely remodeled 2023 west of 41 .Fresh Saltwater heated Pool w/ 6’ Privacy Fenced backyard. 1 miles to Vanderbilt beach, relaxing cottage with NEW screened Lanai, 50 inch HD tv, gas grill, ceiling fans and wet bar with refrigerator for outdoor living. Great house for small families or couples. Both rooms have king beds, so ideal for 2 couples. A new sofa sleeper has been added to sleep 6. Quartzite countertops with travertine floors .

May 25 – Jun. 1

$436 CAD per night

Guest favourite

Home in Matlacha

5.0 out of 5 average rating, 142 reviews

The Secret Island Retreat HeatedPool/4b/open water

Free Heated Pool with open Panoramic Bay Views with Amazing Sunsets from this open layout with 4 bedrooms , a den, 3 bath, 2 car garage. 3200 sq ft. 2nd floor has an oversize owners suite with picture windows over the bay and provides an abundance of space for sitting area or quiet space. Three guests rooms + den. Don't forget to relax & enjoy the breeze on the 2nd story balcony...the perfect retreat. Kayaks, 2 boat lifts, fishing poles, bicycles, games, Grill and much more.

Nov. 24 – Dec. 1

$774 CAD per night

Guest favourite

Home in Matlacha

4.98 out of 5 average rating, 184 reviews

Matlacha Paradise! NEW Waterfront Home-Free Kayaks

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 & 2 person kayaks 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.

Jun. 23 – 30

$282 CAD per night

Guest favourite

Cabin in Bonita Springs

4.9 out of 5 average rating, 247 reviews

Romantic River Cabin for 2; Beautiful Nature View

Beautifully furnished & decorated cabin for 2 located on the Imperial River. High ceilings w/ large windows with Plantation Shutters for fabulous viewing of the serene river. Enjoy the beauty & privacy of the surrounding landscape as your worries drift away. Jump on a kayak & paddle downstream to the Gulf or head upstream & enjoy nature's bounty. Dine outside under the lights or head to Old Bonita for dinner. Calming, quiet and quaint this is a fabulous getaway for 2!

Jun. 16 – 23

$208 CAD per night

Guest favourite

Home in Naples

4.97 out of 5 average rating, 59 reviews

Three Palms Oasis - 2 Miles to Beach and 5th Ave

Brand new listing! We invite you to stay at this stylish, yet affordable luxury home with a gourmet kitchen right in the heart of central Naples. Three Palms Oasis is located in a quiet coastal neighborhood under two miles from the best that downtown Naples has to offer including the sugar white sand beaches, Naples Design District, dining and shopping on 5th Ave, Naples Zoo, Olde Naples, and so much more! You won’t find a better value in the prestigious 34102.

Jun. 12 – 19

$290 CAD per night

Guest favourite

Home in Bonita Springs

4.9 out of 5 average rating, 29 reviews

Bonita Beach Beauty

Relax with the whole family at this peaceful place to stay in Bonita Shores. Walking distance to Bonita Beach (1.1 mile), this charming home is close to North Naples, gulf beaches, shopping, restaurants, and mini-golf. Includes access to paddleboards, kayaks (guest must supply transportation to water) and bikes. Beach chairs and umbrella also included. Book this 2 bedroom, 1 bath home for your next South West Florida getaway! (Small pets may be considered)

May 25 – Jun. 1

$208 CAD per night

Guest favourite

Cottage in Marco Island

4.95 out of 5 average rating, 128 reviews

Waterfront View, private sitting porch

Off the beaten path, of Marco Island, on the beautiful island of Goodland! Beautiful waterfront property.. The space is a one bedroom, one bathroom. Offering you a complete private getaway. Come enjoy a unique stay, overlooking the Everglades. Plenty of room for your boat and trailer, safe overnight dockage available. Witness the magical colors of sunrises sunsets, on a very private piece of paradise. A One of a kind view of the Everglades.

Sep. 20 – 27

$305 CAD per night

Guest favourite

Cottage in North Fort Myers

4.94 out of 5 average rating, 172 reviews

Cozy Private Pool Cottage

This is a small separate guest house with a large pool just steps from the door. Located in a very safe and quiet secluded neighborhood with only 18 homes, all retirees and famous artists along the caloosahatchee with some Riverfront views from pool deck. Only 1.2 miles to Historic Downtown Fort Myers and Edison Museum, along with numerous downtown events, restaurants and nightlife.

Jul. 14 – 21

$230 CAD per night