Vacation rentals with a kayak in Naples

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Top-rated kayak rentals in Naples

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Guest favorite

Home in Cape Coral

4.99 out of 5 average rating, 175 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!

Sep 9 – 16

G$102,434 GYD per night

Guest favorite

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

G$87,202 GYD per night

Guest favorite

Guest suite in Matlacha Isles-Matlacha Shores

4.84 out of 5 average rating, 316 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!

Sep 25 – Oct 2

G$18,932 GYD per night

Guest favorite

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!

Jan 9 – 16

G$60,243 GYD per night

Guest favorite

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 .

Sep 2 – 9

G$58,885 GYD per night

Guest favorite

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.

Jun 9 – 16

G$119,252 GYD per night

Guest favorite

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

G$35,893 GYD per night

Guest favorite

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

G$25,758 GYD per night

Guest favorite

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.

Oct 6 – 13

G$41,765 GYD per night

Guest favorite

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 15 – 22

G$28,777 GYD per night

Superhost

Tiny home in Marco Island

4.87 out of 5 average rating, 249 reviews

Camp Cocktail

Located in quaint Goodland FL on waterfront canal. Walking distance to Goodland Boating Park where you can launch your boat to the gulf and 10,000 Islands. Boat trailer and vehicle parking. Short walk to a vibrant night life at Little Bar, Stan’s, Crabby Lady and Paradise found. Minutes to restaurants and shops on Marco Island.

Oct 6 – 13

G$38,291 GYD per night

Guest favorite

Home in Saint James City

4.98 out of 5 average rating, 174 reviews

Relaxing Waterfront Retreat: 1400 sq ft Home

Discover the charm of Pine Island at our newly renovated 1400 sq. ft. home. Nestled along a serene canal, where you can enjoy the presence of manatees, dolphins, pelicans, and even bald eagles from the comfort of your own private dock. @treasuretrove3070

May 17 – 24

G$29,500 GYD per night