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Vacation rentals with a kayak in Siesta Key

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Siesta Key

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Home in Longboat Key

4.87 out of 5 average rating, 112 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

Boat in Palmetto

4.88 out of 5 average rating, 8 reviews

Fisherman's Paradise - No Cleaning Fee

Come live on a boat at Palm View Marina's Getaway - Your own private Oasis. If you're a local or from out of town and looking for a new experience - this is your personal refuge. Bring your boat! Flop out of your bed and into your vessel. You'll also be in the heart of three tri-area cities: Sarasota, Bradenton, and St Pete you'll be close to many cultural venues that you can visit - plus it is only a hop, skip, and a jump to Tampa. For more info and pics check out Fisherman's Paradise on FB.

Condo in Nokomis

5 out of 5 average rating, 38 reviews

Family Friendly Beach Condo

Property located on Lyon’s Bay, in Nokomis, Florida. This three-bedroom upper Condo unit is situated within a ten minute walk to Nokomis Beach on the Gulf of Mexico. Open kitchen fully equipped, Office area. Wi-Fi Large master suite, second bedroom has a queen bed. Third bedroom features four twin beds, walk-in closet and its own full bath. Your stay comes with access to paddle boards kayaks, which can be launched from a floating dock. Also available for your use are beach chairs and coolers.

Bungalow in Siesta Key

4.89 out of 5 average rating, 9 reviews

Lagoon, pool, the Catamaran at Siesta Key Bungalow

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

Home in Ruskin

4.93 out of 5 average rating, 71 reviews

Silverking Keys Retreat!

Come stay and play at this beautiful 2 bedroom 2 bathroom house (only 1st story) located right on the Tampa Bay! It faces downtown Tampa and St. Petersburg. You can cook breakfast and view the bay straight from the kitchen dinette. The property is located on a dead end street. Fish, and star-gaze from two private docks, one being a two-story. Fish, kayak, snorkel, and you can bring your own boat! A natural sanctuary for dolphins, manatees, red fish, blue herring, snook, ospreys, and eagles!

Condo in Sarasota

4.98 out of 5 average rating, 42 reviews

Gulf View Oasis! 2 BR on Canal-Htd Pool-Kayak/SUP

Gulf View, Top-Floor Beach Condo! Escape to Paradise March 1-15 2 week minimum only Looking for a serene winter getaway to escape the cold? Look no further than our cozy coastal retreat – a tranquil haven where relaxation meets adventure! Tucked away along a quiet canal, this two-bedroom retreat offers everything you need for a refreshing winter escape. Tandem Kayak & paddleboard included! Heated pool! Small, quiet complex! Less than 1/2 mile to Turtle Beach and the free trolley!

Home in Sarasota

4.93 out of 5 average rating, 15 reviews

Beautiful MidCentury Modern Home

Our charming 2BR/2Bath mid-century modern home just steps from the water. Explore Sarasota's beautiful mangroves and beaches with our kayak or bicycle to nearby attractions. Enjoy the open floor plan, modern kitchen, and comfortable living room with sectional couch and TV. The primary bedroom offers a queen bed and office space. The second bedroom has a full bed and TV. Recently remodeled bathrooms and a separate laundry room add convenience. Siesta Key Beach is only six miles away. No pets.

Condo in Sarasota

5 out of 5 average rating, 20 reviews

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

This unique 2 bedroom/ 2 bath condo is right on the waterfront in Siesta Key! It is the upper condo of a two story complex that has a perfect view and feels like your own personal getaway! It comes with a full kitchen, living room, and two decks. Part of what makes it amazing is the private dock on the Pass. Perfect for kayaking and exploring! Or maybe you'd like to just relax and take a dip in the heated pool? Located in the quiet end, you can enjoy the calm, or head to Siesta Village!

Tiny home in Sarasota

4.96 out of 5 average rating, 323 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)

Townhouse in Sarasota

4.77 out of 5 average rating, 135 reviews

Peaceful Oasis: King Bed & Incredible 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.

Vacation home in Venice

4.83 out of 5 average rating, 127 reviews

🌟Venice Cute Pool Villa with bikes Kayaks 🌈🐬

Escape to our charming Venice pool home, where relaxation meets adventure! Perfectly located near the water, this tranquil three-bedroom retreat is nestled on a quiet, palm-lined street. Enjoy easy access to bikes and kayaks for exploring, plus all the beach essentials: cooler, umbrella, and chairs. The pool awaits for sunny days and peaceful evenings (note: a brand-new pool cage is on its way, expected in December). Book now to experience Venice’s beauty from your private oasis!

Home in Venice

4.95 out of 5 average rating, 131 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

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Siesta Key kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Nokomis

4.89 out of 5 average rating, 19 reviews

Vacation sunny 2 miles beach home

Home in Bradenton

4.96 out of 5 average rating, 69 reviews

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Kingbed

Home in Bradenton

5 out of 5 average rating, 66 reviews

Waterfront Home w/ Private Dock, Kayaks, and Yard!

Home in Holmes Beach

4.93 out of 5 average rating, 41 reviews

Backyard Bliss Anna Maria Island

Home in Palmetto

5 out of 5 average rating, 21 reviews

The Ocean Pearl

Home in Bradenton

4.97 out of 5 average rating, 37 reviews

15 Min to Beach Entire Home! Gracies Cottage

Home in Bradenton

5 out of 5 average rating, 14 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

Home in Sarasota

5 out of 5 average rating, 15 reviews

Modern 3 Bed 2 Bath House Backyard + Pet Friendly

Cottage rentals with a kayak

Cottage in Pass-a-Grille Beach

4.8 out of 5 average rating, 266 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Steps To The Beach, Private & Heated Pool, Renovat

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Anna Maria Cottage w/Golf Cart

Cottage in Pass-a-Grille Beach

4.87 out of 5 average rating, 164 reviews

Sunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes

Cottage in Sarasota

4.96 out of 5 average rating, 75 reviews

Cottage by the Bay - free Level 2 EV charging

Cottage in Anna Maria

4.89 out of 5 average rating, 35 reviews

Snail's Pace: On Canal, Kayaks & Dog Friendly

Cottage in Nokomis

4.99 out of 5 average rating, 69 reviews

New Pool Tropical Waterfront Dock & Optional Boat

Quick stats about vacation rentals with a kayak in Siesta Key

Total rentals
40 properties
Nightly prices starting at
$110 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