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

Apartment in Saint James City

4.93 out of 5 average rating, 84 reviews

Island Castaway--Free Kayaks

This is the perfect place to sit back, relax and enjoy the view. You have the privacy of a one-bedroom apartment with small kitchen and bath. We are close to great restaurants and some of the best music on the island. Open water and excellent fishing are minutes away. Two kayaks are set up for fishing and are available for guests to use so bring your fishing rod. Pine Island has no beachs, but Ft Myers Beach is about an hour away or take a ferry ride from Bokeelia to Cayo Costa for the day.

Apr 24 – May 1

G$23,863 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

Cottage in Saint James City

5.0 out of 5 average rating, 27 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!

Oct 21 – 28

G$33,387 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.

Oct 29 – Nov 5

G$48,177 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 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

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 1 – 8

G$26,332 GYD per night

Guest favorite

Home in Bonita Springs

4.9 out of 5 average rating, 31 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 30 – Jun 6

G$24,264 GYD per night

Superhost

Apartment in Matlacha

4.81 out of 5 average rating, 43 reviews

Studio#3 The Heart of Matlacha

It's rare to find a place that's both historic and one-of-a-kind. It’s even rarer to find a place that is historic, unique, romantic, and on a wildlife marine reserve. This newly redone apartment studio unit is part of The Matlacha Cottages. This unit will have a mini kitchenette w/ a refrigerator, microwave, washer and dryer. If you would like to book the entire cottage please also book the back green unit 4. https://www.airbnb.com/h/watercolorsuite

Oct 5 – 12

G$22,597 GYD per night

Guest favorite

Home in Fort Myers

4.92 out of 5 average rating, 85 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!

Jun 5 – 12

G$29,502 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