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Vacation rentals with a kayak in Sarasota

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Sarasota

Guests agree: these kayak rentals 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

Home in Apollo Beach

4.98 out of 5 average rating, 124 reviews

5 Bed/4 Bath Waterfront "Lay Low" in Apollo Beach

Apollo Beach Waterfront Home with Pool & Hot tub, 4 bedroom-4 private baths & elevator. Theater room-murphy bed (5th bedroom). Game room - pool, air hockey... Enjoy kayaks, paddle boards, fish at the dock or book a boat charter with owner, 20% off for guests. 3 restaurants - walking distance. Apollo Beach - 1/2 mile away! Bahia Beach -2 restaurants and EG Simmons Beach - 20 min away. Bring your boat, dock at house, Apollo Beach Marina - 2 min. away. Animal-free home due to severe allergies.

Home in Bradenton

4.97 out of 5 average rating, 110 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 suite in Sarasota

4.94 out of 5 average rating, 504 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 Englewood

4.89 out of 5 average rating, 116 reviews

Free kayak/bikes/walk to beach/full cottage #1

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

Tiny home in Sarasota

4.96 out of 5 average rating, 311 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 suite in Englewood

4.98 out of 5 average rating, 187 reviews

Blue Cottage Suite- Peaceful Old Englewood Charm!

This charming rental is in historic Old Englewood right at the edge of Lemon Bay. The Blue Cottage is in a quiet neighborhood just 4 blocks from Dearborn Avenue with all great entertainment, eclectic shopping and restaurants, live music, and more. The rental includes use of bikes and kayaks. Kayaks are kept at 998 Oxford Dr. We are available to launch or to help you launch kayaks at a local spot. Front porch pictured is part of the main house and is use of this space is not included.

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.

Home in Venice

4.94 out of 5 average rating, 123 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.

Condo in Siesta Key

4.79 out of 5 average rating, 273 reviews

Solitude Suite Studio-Siesta Key-Waterfront Resort

***We pay your AIRBNB fee in this suite! *** Welcome to the Solitude Suite Studio, on Siesta Key. Located in the Solitude Suites on Siesta Key, an adorable small waterfront resort! This is the perfect getaway for 2 people in 1 king bed. Ground floor. Steps to the shared heated pool, Tiki Hut & waterfront dock area. Everything is new! Featuring a 65” smart TV, your own A/C, a king sized bed, full bathroom w/shower, coastal decor, closet & kitchenette.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Sarasota kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Bradenton

4.95 out of 5 average rating, 128 reviews

Historic Wares Creek 3 bedroom with dock access

Home in Ellenton

5 out of 5 average rating, 31 reviews

The Pink Riverhouse- No damage from Hurricanes

Home in Placida

5 out of 5 average rating, 60 reviews

Lu's Lookout~A Beachfront Beauty🤎🌊 🏝 LGI

Home in Ellenton

4.93 out of 5 average rating, 15 reviews

Waterfront Oasis

Home in Bradenton

4.94 out of 5 average rating, 158 reviews

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

Home in St. Petersburg

4.89 out of 5 average rating, 106 reviews

Ocean Breeze bungalow

Home in Sarasota

4.89 out of 5 average rating, 90 reviews

Oceanfront home w/sunset views of Sarasota Bay

Home in Englewood

4.88 out of 5 average rating, 48 reviews

New Listing! Resort-like Oasis on Canal

Cottage rentals with a kayak

Cottage in Pass-a-Grille Beach

4.8 out of 5 average rating, 256 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Anna Maria Cottage w/Golf Cart

Cottage in Englewood

4.88 out of 5 average rating, 133 reviews

Free bikes/kayaks/walk to beach/2bed/2bath #2

Cottage in Englewood

5 out of 5 average rating, 23 reviews

The Coastal Oasis. Only 8 minutes from the Beach!

Cottage in Placida

4.98 out of 5 average rating, 41 reviews

Escape to a Hidden Gem, Beach Cottage on LGI

Cottage in Englewood

4.89 out of 5 average rating, 167 reviews

Free Kayaks! Waterfall Pool! Beach! am

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Steps To The Beach, Private & Heated Pool, Renovat

Cottage in Sarasota

4.96 out of 5 average rating, 74 reviews

Cottage by the Bay - free Level 2 EV charging

Cabin rentals with a kayak

Cabin in Port Charlotte

4.97 out of 5 average rating, 29 reviews

Unique loft experience for motorcycle enthusiasts

Cabin in Arcadia

5 out of 5 average rating, 41 reviews

Waterfront Retreat- w/Kayaks & Peace River access

Cabin in Ruskin

4.75 out of 5 average rating, 4 reviews

River Cabin Million Dollar View! New Management!

Cabin in Arcadia

5 out of 5 average rating, 13 reviews

Riverfront Cabin W/ Kayaks

Quick stats about vacation rentals with a kayak in Sarasota

Total rentals
50 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool

Destinations to explore