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Holiday rentals with a kayak in Siesta Key

Find and book unique kayak rentals on Airbnb

Top-rated Accommodation with a Kayak in Siesta Key

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

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Home in Longboat Key

4.86 out of 5 average rating, 110 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Guest favourite

Home in Bradenton

4.97 out of 5 average rating, 109 reviews

WOW-King Bed w/86° Pool, Turf Golf green, Beaches

Location!! Have fun with the whole family at this stylish home. Just minutes to Anna Maria Island beaches. This incredible newly built home sets the highest standards of luxury living. It’s the ideal retreat with its expansive views of the outdoors from the moment you enter. Open concept with large French doors throughout the home creates the perfect indoor-outdoor lifestyle. Spend the day lounging by the heated pool with a cold drink in your hand. Fun turf yard area with games and putting green

Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 503 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

Condo in Siesta Key

4.82 out of 5 average rating, 267 reviews

Siesta Key 1/1 King bed “Sunset Suite” Pool Kayaks

We pay your AIRBNB service fees for you! Updated & inviting coastal getaway, located on the island of Siesta Key in a small resort called Solitude Suites on Siesta Key. The “Sunset Suite” has a living/dining/kitchenette area w/ 65” TV, a separate bedroom & a separate bathroom. Off the bedroom is a private open wood deck. Table & chairs allow you to enjoy the perfect view of a Siesta Key sunset. New shower in Dec 2023! 2 min drive or 10 min walk to beach! Enjoy FREE Kayaks, SUPs & Tiki Huts!

Cottage in Pass-a-Grille Beach

4.8 out of 5 average rating, 254 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Welcome to your perfect beach getaway! This charming cottage rental is just steps away from the beach. With a queen bedroom, private porch, and cozy living room, it's the perfect space for a couple or solo travelers. A fully equipped kitchen, living area, bedroom, and dining space. Step outside onto the upstairs porch/patio and you'll find the perfect spot to relax with a cold drink and take in salt air. Your downstairs patio is equipped with a BBQ grill and seating for a nice outdoor dinner.

Guest favourite

Tiny home in Sarasota

4.96 out of 5 average rating, 310 reviews

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

Guest favourite

Guesthouse in Downtown Sarasota

4.97 out of 5 average rating, 438 reviews

Quick and Easy Walk Downtown - Tons of Amenities

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

Townhouse in Sarasota

4.77 out of 5 average rating, 131 reviews

Peaceful Oasis: King Bed & Incredible Views

You have arrived, upon entering you will go upstairs to your spacious duplex. You will be greeted by an amazing view of the intercoastal waterway. You will love kayaking on the waterway & seeing all the amazing wildlife. You can sit on your downstairs patio with a cup of coffee or you can take a stroll to Turtle Beach & enjoy the sunset. Hop aboard the trolley & go to the Village & eat and drink at one of our famous restaurants or one of our favorite hot spots. See Guidebook.

Guest favourite

Holiday home in Venice

4.83 out of 5 average rating, 125 reviews

🌟Venice Cute Pool Villa with bikes Kayaks 🌈🐬

Escape to our charming Venice pool home, where relaxation meets adventure! Perfectly located near the water, this tranquil three-bedroom retreat is nestled on a quiet, palm-lined street. Enjoy easy access to bikes and kayaks for exploring, plus all the beach essentials: cooler, umbrella, and chairs. The pool awaits for sunny days and peaceful evenings (note: a brand-new pool cage is on its way, expected in December). Book now to experience Venice’s beauty from your private oasis!

Guest favourite

Home in Venice

4.95 out of 5 average rating, 121 reviews

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks

Welcome to our Mid Century Modern waterfront getaway on the highly sought after Curry Creek. Perfectly situation between Nokomis Beach (2 miles) and Venice Beach (3 miles). Enjoy spending time fishing on the private dock or getting out on the water with our 4 kayaks and slip. We're located a half mile away from The Legacy Bike Trail (we have 6 bikes for guest use). large firepit, charcoal grill, cornhole, tons of supplies for shark teeth hunting and days spent at the beach

Townhouse in Ruskin

4.93 out of 5 average rating, 213 reviews

Waterfront Townhome w/ Heated Pool & Balconies

Relaxation awaits you the moment you step in to Bahia Bungalow, a 2 Bedroom, 1.5 Bath town home nestled in Little Harbor Resort. Little Harbor is located on a partially private guest reserved beach in Ruskin, a short drive from Tampa, Sarasota & St. Pete. The resort overlooks Tampa Bay & features a heated outdoor pool, basketball and pickleball courts, fitness area, a playground & a marina. Dining within the Resort include a bay-view restaurant, a poolside bar/grill.

Guest favourite

Home in Anna Maria

4.94 out of 5 average rating, 167 reviews

Re-Modeled & Now Ready for Post-Hurricane Visits!

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Siesta Key kayak rentals

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

Guest favourite

Home in Ellenton

5 out of 5 average rating, 31 reviews

The Pink Riverhouse- No damage from Hurricanes

Guest favourite

Home in Ellenton

4.93 out of 5 average rating, 15 reviews

Waterfront Oasis

Guest favourite

Home in Coquina Key

5 out of 5 average rating, 17 reviews

Casa Coquina: waterfront, pool, hot tub, boat lift

Guest favourite

Home in Sarasota

5 out of 5 average rating, 11 reviews

Modern 3 Bed 2 Bath House Backyard + Pet Friendly

Home in Bradenton

4.87 out of 5 average rating, 55 reviews

Executive Bayside Retreat/Pool/IMG/Sarasota Bay

Guest favourite

Home in Lido Key

5 out of 5 average rating, 10 reviews

Gorgeous 3/3 Canalfront Home Walk to Lido Beach!

Guest favourite

Home in Sarasota

4.89 out of 5 average rating, 90 reviews

Oceanfront home w/sunset views of Sarasota Bay

Guest favourite

Home in Osprey

5 out of 5 average rating, 28 reviews

Heated Pool | 3 Beds | Near Beaches and parks

Cottages with a kayak

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Steps To The Beach, Private & Heated Pool, Renovat

Guest favourite

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Anna Maria Cottage w/Golf Cart

Guest favourite

Cottage in Pass-a-Grille Beach

4.87 out of 5 average rating, 163 reviews

Sunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes

Guest favourite

Cottage in Ruskin

4.91 out of 5 average rating, 101 reviews

Little Manatee River Cottage

Guest favourite

Cottage in Sarasota

4.96 out of 5 average rating, 74 reviews

Cottage by the Bay - free Level 2 EV charging

Cottage in Ruskin

Amazing on river cottage with dock to fish, kayak!

Guest favourite

Cottage in Nokomis

4.98 out of 5 average rating, 63 reviews

New Pool Tropical Waterfront Dock & Optional Boat

Quick stats about holiday rentals with a kayak in Siesta Key

Total rentals
40 properties
Nightly prices starting at
$167 AUD before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
30 properties have a pool

Destinations to explore