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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, 111 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, 505 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!

Cottage in Pass-a-Grille Beach

4.8 out of 5 average rating, 258 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

4.89 out of 5 average rating, 192 reviews

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

Guest favourite

Guesthouse in Downtown Sarasota

4.97 out of 5 average rating, 439 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.

Guest favourite

Bungalow in Siesta Key

4.94 out of 5 average rating, 16 reviews

Lagoon, Pool, the Sunset at Siesta Key Bungalows

The Siesta Key Bungalows offer a heated pool, courtyard & a dock on Heron Lagoon. A resort with something for everyone. The Sunset Bungalow's airy one bedroom space; has an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed, bathroom, kitchen and a veranda, you'll feel at home. The Sunset is fully stocked with linens, care essentials, plus eating & cooking utensils. An additional single-roll-away-bed allows accommodations for three guests.

Rental unit in Siesta Key

4.85 out of 5 average rating, 230 reviews

Siesta Key - Poolside Suite - Studio - Free kayaks

Poolside Suite is a hotel room style suite. There is a king sized bed & a 65” smart TV. Free Wifi. A private en suite bathroom features a walk in shower, toilet and large vanity with sink & mirror. Also provided in a walk in closet space is a fridge, microwave, freezer, blender, cups, plates, silverware, keurig, iron, mini ironing board & hangers. Simple & stylish! No frills, yet all the necessities! The a/c is a centralized system, set to 71-73 degrees. Fan provided.

Guest favourite

Home in Venice

4.94 out of 5 average rating, 124 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

Guest favourite

Home in Anna Maria

4.94 out of 5 average rating, 167 reviews

New Construction & 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.

Guest favourite

Home in Sarasota

5 out of 5 average rating, 10 reviews

Brand New Pool Home with Boat Dock

Be among the initial guests to relish in the splendor of this charming 3-bed, 2-bath abode overlooking Phillippi Creek, with a rejuvenating pool and fresh, deluxe furnishings. It offers all you need for an unforgettable escape, featuring a well-equipped open kitchen, 2 fun large Roku smart TVs in the living spaces, and a 50" Roku Smart TV in the master bedroom. Essential bathroom amenities are provided for your comfort.

Home in Palmetto

4.78 out of 5 average rating, 144 reviews

Private Efficiency

LONG TERM Guests Welcome! To Check out is 11am Efficiency with fully stocked kitchenette is a living room with Murphy Bed. Living room by day, bedroom by night. Coffee, tea and creamer in stock. 15 minutes to Ellenton Outlet Mall with plenty of dining choices on the way. 30 minutes to St Pete or Sarasota. STRICT LIMIT TO (2) GUESTS, NO SMOKING INSIDE, NO cats No dogs For Local events see realizebradenton dot com

Holiday rentals for every style

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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 Longboat Key

5 out of 5 average rating, 23 reviews

North Shore Six

Home in Anna Maria

4.65 out of 5 average rating, 20 reviews

Sand Trap by Beach Boutique Rentals

Guest favourite

Home in Sarasota

5 out of 5 average rating, 12 reviews

Modern 3 Bed 2 Bath House Backyard + Pet Friendly

Home in Bradenton Beach

4.74 out of 5 average rating, 19 reviews

AMI Cortez Beach Retreat "Views" Resort-style Pool

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 Bradenton

4.93 out of 5 average rating, 54 reviews

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

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 Sarasota

4.96 out of 5 average rating, 74 reviews

Cottage by the Bay - free Level 2 EV charging

Cottage in Sarasota

4.81 out of 5 average rating, 155 reviews

Cozy clean cottage

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
$187 NZD 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