
Vacation rentals with a kayak near Siesta Beach
Find and book unique kayak rentals on Airbnb
Top-rated kayak rentals near Siesta Beach
Guests agree: these stays 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!

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

@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.

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.

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.

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.

Florida Cracker Cabin on cattle ranch/Myakka River
We are located in Myakka City, FL, which is a short drive to Siesta Key and Lido Beach and Sarasota! Enjoy a peaceful stay in our newly built, unique, air-conditioned cracker cabin. The cabin sleeps 4 guests and is located in the middle of our 1,100 acre working cattle ranch. Step outside and you are right on the Myakka River and can sit by the fire-pit at night and enjoy the sounds of nature. While your visiting, enjoy a kayak down the Myakka River.

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 unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

Las Palmas Beach Rentals unit 2
Unit 2 Ground floor;800 sq ft; patio; limited beach view . Steps to the white sandy beach across the street Free parking to registered guest. Fully equipped kitchen with markets nearby, Restaurants and shopping, within walking or hop free trolly. Trolly stop nearby. Linens and basic supplies are included. Overnight guest are welcome to arrive early to adventure the island, stay parked until after sunset on departure day.

Sarasota Waterfront Pool Home with Dock
Welcome to coastal elegance on Palm Island, Sarasota. - 4 bedrooms, 4 baths with modern, open layout - Gourmet kitchen with Italian Fulgor cooktop - Ground-floor master suite for privacy - Sun-filled flex room for work or relaxation - Private dock on a boating-friendly lot - Steps from Siesta Key Beach and Siesta Village - Newly renovated pool and outdoor space - Enjoy waterfront living and island tranquility

Waterfront Pool Home Steps to Beach
Escape to our waterfront oasis on Anna Maria Island! This bright, updated home features a private heated pool, hot tub, and dock. Perfect for families, it's just a 5-minute walk to the world-renowned Gulf beaches. Enjoy stunning sunrises, a dedicated workspace, and modern coastal decor. Explore the island with ease via the free trolley. Your perfect getaway awaits!
Popular amenities for kayak rentals near Siesta Beach
House rentals with a kayak

Heated saltwater pool home - turf putting green

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

Waterfront Retreat | Heated Pool & Boat Dock

4BR, Heated Pool, Pickleball, Basketball near IMG

Holiday-January Stays w/Private 30' Dock & Pool

Sweet Siesta Cottage

Siesta Key Hot Tub Cottage, Sleeps 6. Kid Friendly

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

Sun and Sea Gem on Siesta Key

Renovated Beach Paradise. Ground Floor unit 64

Bayside Escape-Condo w/ Dock, Pool, and Near Beach

Siesta Key 2 miles! Pool, Steps to Dining, +Bikes!

Waterfront w/ Pool, mins to SK Beaches, bikes/sups

Siesta Oak Esc. Luxury on-water house

Gulf View! 2/1 with Heated Pool, Kayaks and SUP

Vintage Coastal
Quick stats about vacation rentals with a kayak near Siesta Beach

Total vacation rentals
Explore 50 vacation rentals in Siesta Beach

Nightly prices starting at
Siesta Beach vacation rentals start at ﺩ.ﺇ331 per night before taxes and fees

Verified guest reviews
Over 1,950 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
50 of Siesta Beach vacation rentals include wi-fi access

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

4.8 Average rating
Siesta Beach stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Luxury rentals Siesta Beach
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- Waterfront rentals Siesta Beach
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- Rentals with a kayak Sarasota County
- Rentals with a kayak Florida
- Rentals with a kayak United States
- Anna Maria Island
- Crescent Beach
- John's Pass
- Raymond James Stadium
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Vinoy Park
- Cortez Beach
- Lido Key Beach
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Manasota Key Beach
- Gulfport Beach Recreation Area
- North Beach
- River Strand Golf and Country Club
- Englewood Beach
- Splash Harbour Water Park
- Myakka River State Park
- North Beach At Fort DeSoto Park
- Don CeSar Hotel
- Point Of Rocks




