We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals with a kayak in Siesta Key

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Siesta Key

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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 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!

Townhouse in Pass-a-Grille Beach

4.88 out of 5 average rating, 213 reviews

Steps to Beach+bikes VaCay getaway on PaG island

Welcome to your island beach escape! This charming coastal abode boasts all the island vibes you need for a relaxing getaway. Enjoy the quaint historic village (5 houses wide) while being just steps away from the most beautiful beach in Florida! Take a stroll through the picturesque streets of Pass a Grille and soak up the old beach charm. The rental home has hardwood floors, a screened-in porch, and a sun patio, 2 bikes to cruise around the area! open-concept kitchen + bar and smart TVs.

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)

Home in Ruskin

4.95 out of 5 average rating, 168 reviews

Private Beach Nature 2 ppl pets Work space remote

Unique, modern beachfront guest house-sits on a MULTI million $ property. Blend of Frank Lloyd Wright & Luis Barragan design. Located on Tampa Bay btwn Sarasota and Tampa/St Pete. Surrounded by palm trees, mangroves, birds chirping, dolphins, manatees, waves gently lapping and breezes. Sand from door to private beach. Fresh sheets, outdoor shower, small fridge, microwave, air fryer, & in and outdoor seating areas. Kayak and paddle board available. SUNRISE'S UNIQUE We are DOG FRIENDLY!

Condo in Ruskin

4.73 out of 5 average rating, 150 reviews

River Delight Studio 109 Tampa Bay Florida Resort

Little Harbor Resort is a paradise packed with amenities. Enjoy 2 pools, Jacuzzi, Beach on Tampa Bay (not Gulf), 2 restaurants, Tiki Bar, tennis, pickleball, basketball, playground, fishing charters, sightseeing cruises, and Freedom Boat Club. The Inn at Little Harbor River Delight Studio is a ground-floor, non-smoking studio which features a kitchenette, fridge, microwave, sink, in counter hotplate, dishwasher, coffee maker with two luxurious queen beds, and captivating island decor.

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.

Vacation 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!

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.

Home in Bradenton

4.94 out of 5 average rating, 158 reviews

4/2 house/pool we have power/wifi/water IMG blake

Welcome to West Bradenton, 3.5 miles away from IMG Academy! Convenient vacation destination just 5 miles away from the beaches, top sites and the best fishing spots! Enjoy nice Florida weather and have best time in this newly and completely renovated 4/2 pool/TIKI bar house with a huge fenced in backyard! We have lounge chairs, hammocks and kayaks for your use! The house is set up to make your vacation relaxing and full of fun. Just bring your swimsuit!

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats 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

House rentals with a kayak

Home in Bradenton

5 out of 5 average rating, 64 reviews

Waterfront Home w/ Private Dock, Kayaks, and Yard!

Home in Holmes Beach

4.93 out of 5 average rating, 41 reviews

Backyard Bliss Anna Maria Island

Home in Venice

4.9 out of 5 average rating, 52 reviews

The Ripple Inn At Fennario

Home in Bradenton

4.87 out of 5 average rating, 55 reviews

Executive Bayside Retreat/Pool/IMG/Sarasota Bay

Home in North Port

4.99 out of 5 average rating, 84 reviews

North Port -Nov/Dec Available - Fish/Canoe/Bike

Home in Bradenton

4.93 out of 5 average rating, 54 reviews

Waterfront w/ Pool, Dock + Paddle/Kayaks | Sea Gem

Home in Sarasota

4.89 out of 5 average rating, 90 reviews

Oceanfront home w/sunset views of Sarasota Bay

Home in Indian Beach-Sapphire Shores

5 out of 5 average rating, 43 reviews

Perfect Family Getaway+ping pong, mini golf, bikes

Cottage rentals with a kayak

Cottage in Pass-a-Grille Beach

4.8 out of 5 average rating, 254 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Steps To The Beach, Private & Heated Pool, Renovat

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Anna Maria Cottage w/Golf Cart

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

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!

Cottage in Nokomis

4.98 out of 5 average rating, 63 reviews

New Pool Tropical Waterfront Dock & Optional Boat

Quick stats about vacation rentals with a kayak in Siesta Key

Total rentals
40 properties
Nightly prices starting at
G$22,934 GYD 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