Vacation rentals with a kayak in Sanibel Island

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Top-rated kayak rentals in Sanibel Island

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Guest favorite

Home in Captiva

5.0 out of 5 average rating, 66 reviews

Beachfront | Pvt Fishing Dock, Shelling, Sunrises

🏝️Latitude Adjustment on North Captiva!! 💎Newly renovated throughout (2023) 👨‍👩‍👦Family Friendly 🏖️Private Beachfront 🎣Private Fishing Dock w/ Lights for night fishing, best fishing spot! Loaded w/ Snook,Redfish,Trout,Sheepshead &more! 🏊‍♂️Island Club Membership (pools,kayaks,bikes) 🏯4-bedroom, 4.5-bath comfortably sleeps 10 ⭐️2,600 sqft under a/c, 1,400 sqft decking overlooking water 📞Owner avail from booking-checkout! 👩‍✈️Prof Managed- Luggage/Grocery Serv 🛻Golf Cart Included! 🛜High Speed Wifi 🕹️Games

Sep 7 – 14

G$134,467 GYD per night

Guest favorite

Home in Captiva

5.0 out of 5 average rating, 11 reviews

Hear the Waves & See the Beach - 1 house to shore

🌊 Amazing beach views 🌅Stunning sunsets from crow’s nest. 🏠 Distinguished island home - professionally designed & extremely comfortable 🛥️Shared boat dock - ask about availability 🛌🏽Westin Heavenly Beds for ultimate comfort and sleep ✅ Gourmet chef's kitchen 🏖️New beach chairs, umbrellas, kayaks, bikes, and outdoor games. 🚙 Golf cart included! 🐶 Pet-friendly! 🧻Supplies, amenities and luxury toiletries provided 💻 High speed internet 😊24/7 local host support - we’re here to make your trip perfect!

Oct 30 – Nov 6

G$117,956 GYD per night

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!

Oct 14 – 21

G$102,537 GYD per night

Guest favorite

Home in Captiva

4.91 out of 5 average rating, 102 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.

Aug 16 – 23

G$118,476 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!

Oct 24 – 31

G$18,890 GYD per night

Guest favorite

Home in Naples

4.94 out of 5 average rating, 105 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!

Sep 20 – 27

G$33,818 GYD per night

Guest favorite

Townhouse in Captiva

5.0 out of 5 average rating, 15 reviews

Ebb Tide on North Captiva Island

Magical beaches. Incredible fishing. Stellar shelling. And so much sunshine! Located on the enchanting island of North Captiva, Florida, in Safety Harbor Club, Ebb Tide is a beautiful home where you can reconnect with nature and disconnect from the hustle and bustle of everyday life. Pristine, natural beaches, ample sunshine and no cars. Travel to the island is by the Island Girl Ferry, boat taxi, or your own boat. This is one of the reasons it is such a pristine paradise.

Apr 12 – 19

G$82,055 GYD per night

Guest favorite

Home in Naples

4.99 out of 5 average rating, 95 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.

Apr 25 – May 2

G$36,035 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.

Jul 23 – 30

G$98,964 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.

May 24 – 31

G$36,740 GYD per night

Guest favorite

Home in Captiva

4.97 out of 5 average rating, 101 reviews

Steps To Private Beach Captiva Retreat Golfcart

PRIVATE ISLAND SUMMER FUN! Welcome to our charming Beach Cottage on North Captiva Island, perfect for families and beach lovers. A stone's throw from the Gulf's pristine beaches, our cottage offers modern comforts, a stocked pantry, and a free golf cart for exploring. Enjoy pet-friendly accommodations (with fees) and easy beach access. Accessible by ferry, boat, or plane, it's the ideal spot for a tranquil yet adventurous summer retreat. STAY WITH US

Nov 19 – 26

G$91,571 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.

Jan 5 – 12

G$28,806 GYD per night