
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.

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

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!

Heated saltwater pool home - turf putting green
Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

Summer House longboat key
Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical 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. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach
The Siesta Key Bungalows offer a heated pool, courtyard, sun loungers, gas-grills, laundry facilities, kayaks & a private dock on Heron Lagoon. The Dolphin Bungalow's one bedroom space; connects a welcoming living room, full-kitchen, and a private backyard patio. A king bed, two HDTVs and a full bathroom will further enhance your overall experience. Fully stocked with linens, care essentials, eating & cooking utensils. A queen sofa bed in the living room, allows for a capacity of three.

@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)

Coolest Downtown Neighborhood - Ebikes, Beach Gear
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.

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool
Whisk your favorite person away to BayDreaming! Escape to this quiet 1BR/1.5BA Siesta Key condo - just an 8-minute walk to Turtle Beach! Perfect for couples, it features a private deck with canal and Gulf views , a heated pool for sunset swims, 2 supyaks and a plush king bed for cozy nights in. Enjoy garage parking, beach gear, and a peaceful, welcoming community. Whether you're here to relax or reconnect, this coastal retreat offers the perfect mix of romance or just plain serenity!

Relaxing Retreat, King Bed, Beautiful Scenic 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.

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.

AMI favorite w/Private 30' Dock & Pool
* 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.

~ Relax Here 2 BED Home 8 Min to Beach ~
Enjoy a bright Florida getaway just 8 minutes from the beach! Perfect for families or couples, our cozy home features fast Wi-Fi, a fully equipped kitchen, free parking, and all the essentials for a relaxing stay. Close to restaurants, local shops, and water activities, this is the ideal base for your Florida vacation. Book now for convenience, comfort, and easy access to Gulf Coast fun!
Popular amenities for Siesta Key kayak rentals
House rentals with a kayak

The Shore House Private Dock Hot Tub

Complete Privacy Mid Century 2mi to #1 Beach Pool

Historic Wares Creek 3 bedroom with dock access

New! Boat Dock + Dolphins + Beaches + Hot tub!

Walk to Bay & DTWN, Lido Beach/St. Armand's 3.9 mi

Water Access Retreat | Kayaks + Hot Tub

Heated Pool & spa! 250 steps to beach!

Private Island Old FL Waterfront Heaven on Earth
Cottage rentals with a kayak

Anna Maria Cottage w/Golf Cart

Lido Key Beach Bungalow with Private Heated Pool!

New Country Cottage on Lake Manatee Lakewood Ranch

Cottage & Tree ~ by the Sea

2/2 Charming Riverfront Cottage w Deck & Kayaks

Steps To The Beach, Private & Heated Pool, Renovat

Cottage by the Bay - free charging, Level 2 EV

Siesta Key Cozy Cottage across from the beach!
Other vacation rentals with a kayak

Renovated Beach Paradise. Ground Floor unit 64

Cedar Sunsets-4 bed, 4 bath, 4 Houses to the beach

Dockside 1-Bed Villa

Sarasota Luxury house, 3BD, Siesta Key Beach

Intracoastal Connections-Incredible Sunsets-Luxury

Waterfront, Resort Pool / Spa, & Fitness Center!

Walk to beach/village, boat lift, monthly discount

Waterfront Suite-20 min to Gulf Beaches
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,014 | ﺩ.ﺇ1,726 | ﺩ.ﺇ1,825 | ﺩ.ﺇ1,238 | ﺩ.ﺇ1,072 | ﺩ.ﺇ1,010 | ﺩ.ﺇ1,010 | ﺩ.ﺇ959 | ﺩ.ﺇ1,050 | ﺩ.ﺇ1,234 | ﺩ.ﺇ757 | ﺩ.ﺇ1,076 |
| 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 |
Quick stats about vacation rentals with a kayak in Siesta Key

Total vacation rentals
Explore 70 vacation rentals in Siesta Key

Nightly prices starting at
Siesta Key vacation rentals start at ﺩ.ﺇ514 per night before taxes and fees

Verified guest reviews
Over 2,260 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
70 of Siesta Key vacation rentals include wi-fi access

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

4.9 Average rating
Siesta Key stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a kayak Sarasota County
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Raymond James Stadium
- John's Pass
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
- Cortez Beach
- Anna Maria Public Beach
- Bean Point Beach
- Jannus Live
- Manasota Key Beach
- River Strand Golf and Country Club
- Englewood Beach
- Gulfport Beach Recreation Area
- Splash Harbour Water Park
- Myakka River State Park
- North Beach At Fort DeSoto Park
- The Don CeSar
- Lakewood National Golf Club




