
Holiday rentals with a kayak in Sarasota
Find and book unique kayak rentals on Airbnb
Quick stats about holiday rentals with a kayak in Sarasota

Total holiday rentals
Explore 50 holiday rentals in Sarasota

Nightly prices starting at
Sarasota holiday rentals start at €44 per night before taxes and fees

Verified guest reviews
Over 2,130 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
50 of Sarasota holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Sarasota rentals

4.9 Average rating
Sarasota stays are highly rated by guests – averaging 4.9 out of 5!

Nearby attractions
Sarasota’s top spots include Bayfront Park, Marie Selby Botanical Gardens and Sarasota Jungle Gardens
Top-rated rentals with kayak in Sarasota
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool
Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available
4.96 out of 5 average rating, 123 reviews
Near Anna Maria Island Beach-Studio on Wares Creek
This place delivers ample living space,latest amenities, and quick,easy access to Coastal Water,Anna Maria Island Beaches,and city Down Town. Spacious,bright,and tastefully furnished,with great screened porch,cozy gazebo,sparkling heated swimming pool . We supply 2 kayaks and everything that you might need to spend a day at the beach or on the water.We also supply fishing rods(adults and kids) and bait bucket. We can take you on a coastal trip in our boat if you wish (extra charges will apply )
4.94 out of 5 average rating, 126 reviews
River Cottage 2/2 - Kayaks & Huge Deck-Old Florida
Old Florida charm meets peaceful riverfront living at the Lazy Gator Lodge. This unique Braden River getaway features two spacious king en suite bedrooms, an open-concept living area, fully stocked kitchen, massive waterfront deck, & fenced yard perfect for pets. Guests can explore the river by kayak and paddle to local waterfront restaurants and live music spots. Centrally located near Lakewood Ranch, UTC, Bradenton and Sarasota — plus the white sand beaches of Siesta Key & Anna Maria Island.
4.97 out of 5 average rating, 73 reviews
Heated Pool - Just 1 mile to Beach! Updated/Fun!
Fun for the whole family!! Only 1 mile to the Beach! This newly updated home comes fully furnished with 4 bedrooms and 3 bathrooms. With a total of 6 beds, the home sleeps 10 comfortably. The Heated Pool is perfect for swimming, and being only 1 mile to the world famous Siesta Key Beach Access 12, this home also makes beach going easy and convenient. Inside, the home is clean, spacious and newly updated and equipped with smart tvs, air hockey table, pool table foose-ball, Pac-Man - fun for all
4.92 out of 5 average rating, 124 reviews
LG Beach Bungalow on Gulf w/Bay Access & deck too!
Welcome to Golden Girl. Our 3 bedroom 2 bath home is totally renovated with all new furniture. A 2nd level observation deck, private hot tub, bunkroom sleeps 6, two bdrms with kings, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, smart TV's, so much more! Lanai opens up to semi private beach and a quiet neighborhood of single family homes. There is Bay access too. Kayaks available for rent. There is a separate apartment above not included. The location cannot be beat!
4.83 out of 5 average rating, 122 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)
4.95 out of 5 average rating, 425 reviews
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ heated pool, kayaks, table tennis & Tiki Huts. * Just a 10-12 min walk to award winning beach. *1 Bedroom w/King bed. *1 full bathroom w/shower. *Large kitchen, open living room, fully furnished inc towels & linens. *Private lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!
4.87 out of 5 average rating, 314 reviews
Bay Breeze Cottages #2
Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.
4.88 out of 5 average rating, 207 reviews
River House with Kayaks. Relax on the River.
Grab a kayak, and hop on the river for a chance to see some of Florida's wildlife. Birds, otters, and alligators! The Riverhouse is a one of a kind vacation home. A fully equipped kitchen, living Rm with leather couches and a dining area. 3 bdrms- a King in the Master, 2 twins in 2nd and a bunk rm, 2 full baths, a balcony, and 2 patios. Situated on a quiet cul-de-sac, only 5 mins from I-75 and 10 mins from UTC Mall, Benderson race park, and exceptional dining experiences.
5.0 out of 5 average rating, 125 reviews
Stunning Bay Waterfront! Jaw dropping Water Views!
Spectacular Lemon Bay views! Upstairs at Blue Island Inn, waterfront “Bella Vista” with Bay & Pool views! 2 bedrooms; kitchenette & family room. Enjoy “Lemon Bay-front beach” in backyard. Low-key quiet vacationers. 1 car parking spot. No visitor parking. Free 2 kayaks. Login to your favorite streaming services with Smart TVs. Beautiful Blind Pass Beach, Englewood Beach, 5 restaurants & Tiki Bars are just 1.5 mile away or hop on Stumpy's Free Shuttle (tip based)
4.99 out of 5 average rating, 143 reviews
Sunset and beach view from your balcony Unit 403
A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.
4.88 out of 5 average rating, 139 reviews
New Pool Tropical Waterfront Dock & Optional Boat
Located on a highly desirable street, the house is perched high above Curry Creek offering spectacular water views from every room. The property includes a boat ramp to avoid the public launch. Three kayaks (two tandems and one single). Two miles from Nokomis Beach and only half a mile from The Legacy Bike Trail. You can do so many fun things, or just have a drink on the dock and watch the manatees. Pet Friendly
4.96 out of 5 average rating, 112 reviewsPopular amenities for kayak rentals in Sarasota
House rentals with a kayak

Private Island Old FL Waterfront Heaven on Earth
4.98 out of 5 average rating, 124 reviews
Xanadu|Fishing/ Pool/Dock|Kayaks|Bar/Gazebo/ Kids
5.0 out of 5 average rating, 106 reviews
Sea Gem | Waterfront Oasis w/ Pool, Dock + Kayaks
4.92 out of 5 average rating, 103 reviews
Modern 4bd | Heated Pool | Hot Tub + Studio Suite!
5.0 out of 5 average rating, 23 reviews
Winter Haven Retreat – Steps to Bay & Ringling
4.98 out of 5 average rating, 83 reviews
Beachfront Escape + Private Deck
4.78 out of 5 average rating, 9 reviews
Fish/Canoe/Kayak/Pool | AMI | Siesta | 5mi 2 IMG
4.86 out of 5 average rating, 69 reviews
Waterfront 5BR w/Pool, Spa, Boat Lift, Putting Grn
4.96 out of 5 average rating, 25 reviewsCottage rentals with a kayak

Siesta Key Cozy Cottage across from the beach!
4.91 out of 5 average rating, 208 reviews
Unit #2 Free bikes/kayaks/walk to beach/2bed/2bath
4.9 out of 5 average rating, 211 reviews
Steps2Beach-Walk everywhere-Bikes & gear Included
4.89 out of 5 average rating, 193 reviews
Little Manatee River Cottage
4.9 out of 5 average rating, 152 reviews
Private Beach-Luxury 4BR+SUPs&Kayaks-Pets-BBQ
5.0 out of 5 average rating, 38 reviews
Island Getaway, Beach House, Dock, Pet Friendly
4.99 out of 5 average rating, 79 reviews
Serene Island Cottage Waterfront Haven
4.74 out of 5 average rating, 137 reviews
New Country Cottage on Lake Manatee Lakewood Ranch
4.93 out of 5 average rating, 29 reviewsCabin rentals with a kayak

Waterfront Retreat- w/Kayaks & Peace River access
5.0 out of 5 average rating, 69 reviews
Unique loft experience for motorcycle enthusiasts
4.98 out of 5 average rating, 45 reviews
Luxury Cottage|6PPL|Pool| Game Room| Kayaks| BBQ
New place to stay
Glamping on the Myakka River in the Prairie Cabin

Riverfront Cabin W/ Kayaks
4.97 out of 5 average rating, 66 reviewsWhen is the best time to visit Sarasota?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €172 | €191 | €223 | €151 | €171 | €175 | €113 | €118 | €122 | €131 | €132 | €151 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
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