
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.

Bayside Escape-Condo w/ Dock, Pool, and Near Beach
This 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 w/ a sofa-bed, 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!

Private Island Old FL Waterfront Heaven on Earth
Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

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!

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.

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach
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 private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. An additional queen sofa-bed allows accommodations for three guests.

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.

Luxury Waterfront Home in Sarasota w/ Pool & Dock
Exclusive Amenities Include: • Private Heated Saltwater infinity-edge Pool & Spa • Canal front with Breathtaking Intracoastal Views • 4 Bedrooms - 2 Primaries with Ensuite Bathrooms for a total of 3 Full Baths • Outdoor Lounge Area - Private Heated Pool with Baja Shelf, Gas Grill & Outdoor Kitchen • Private Boat Dock • Dock Fishing • Free WiFi & HD Smart TV’s • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs, Cooler, & Cart

Waterfront Retreat | Pool • Spa • Dock | Bridge St
🌴 Anna Maria Island Waterfront Oasis! Private dock + heated pool included. Relax by the pool, sip coffee on the dock, or walk just 5 minutes to the Gulf’s sugar-sand beach. Bright, updated home with stocked kitchen, fast Wi-Fi, smart TVs, and cozy beds—perfect for families or couples. Grill by the pool, dine outdoors, or fish from the dock. Boat/kayak friendly. Beach gear + parking included. Your peaceful island escape awaits.

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

Villa Champagne | Pool, Spa, Dock, Walk to Beach
🦩Exclusive Amenities Include: • Private Heated Pool & Spa • 0.4 Miles to Siesta Key Beach • 0.3 Miles to Siesta Key Village • Canal-Front with Private Dock • Gourmet Kitchen with Large Island • 4 Bedrooms, 3.5 Baths • Balcony Access from Multiple Rooms • Outdoor Grill + Alfresco Dining • High-Speed Wi-Fi • In-House Washer/Dryer • Starter Packs of Essentials for Kitchen and Bath • CottageClean™ Certified
Popular amenities for kayak rentals near Siesta Beach
House rentals with a kayak

Heated saltwater pool home - turf putting green

The Shore House Private Dock Hot Tub

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

Waterfront Retreat | Heated Pool & Boat Dock

Summer House longboat key

Siesta Retreat - 513

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

King Bed/Pool/Game Room/Fire Pit/Hammock/Near AMI
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

SeaScape

Renovated Beach Paradise. Ground Floor unit 64

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

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

Ramada by Wyndham Sarasota Waterfront- Bar & Grill

Waterfront Suite-20 min to Gulf Beaches

The Village Breeze I- Heated Pool, Walk to Beach!

Cozy Condo in Siesta key with boat dock
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 R1,538 ZAR 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
- Apartment rentals Siesta Beach
- Rentals with beach access Siesta Beach
- Rentals with pools Siesta Beach
- Beach house rentals Siesta Beach
- Family-friendly rentals Siesta Beach
- Pet-friendly rentals Siesta Beach
- Waterfront rentals Siesta Beach
- Condo rentals Siesta Beach
- Rentals with an EV charger Siesta Beach
- Villa rentals Siesta Beach
- Rentals with a fireplace Siesta Beach
- Luxury rentals Siesta Beach
- Townhouse rentals Siesta Beach
- Rentals with a sauna Siesta Beach
- Fitness-friendly rentals Siesta Beach
- Rentals with a washer and dryer Siesta Beach
- House rentals Siesta Beach
- Rentals with lake access Siesta Beach
- Rentals with a patio Siesta Beach
- Rentals with a hot tub Siesta Beach
- Beachfront rentals Siesta Beach
- Rentals with breakfast Siesta Beach
- Rentals with a fire pit Siesta Beach
- Cottage rentals Siesta Beach
- Rentals with outdoor seating Siesta Beach
- 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
- Cortez Beach
- Lido Key Beach
- Vinoy Park
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- North Beach
- River Strand Golf and Country Club
- Manasota Key Beach
- Englewood Beach
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park
- Don CeSar Hotel
- Point Of Rocks
- Lakewood National Golf Club




