
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.

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.

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

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 Cozy Cottage across from the beach!
Adorable totally renovated !!!Siesta key cottage one block from the beautiful white sand beach and two blocks from the iconic Siesta Key Village on the north end of the island. Everything is a short walk including all the shops and restaurants of Siesta Village. Very private fenced in yard with plenty of comfy furniture and barbecue:) Very nice size stainless steel/granite kitchen with a dining room and a large sunken living room. Both the living room and the bedroom open to the private patio!

Lido Key Beach Bungalow with Private Heated Pool!
Behind the privacy wall you will discover an oasis in this beautiful beach bungalow. The outside space is amazing and almost as large as the inside space. Your own private pool and covered lanai area is the perfect place to relax, gather for dinner, watch TV and just enjoy outside living. You are a two minute walk to the beautiful sands of Lido Beach. St. Armand's Circle is a 10 minute walk for shopping and dining. Kayaking is a 2 minute walk and you can spend the afternoon exploring!

Manatee Cove: Waterfront Oasis w/GameRoom &HotTub
Welcome to Your Private Waterfront Oasis! This spacious home on a serene canal off Sarasota Bay features 3 bedrooms, 2 bathrooms & a HUGE climate-controlled game room! Enjoy direct water access for fishing, canoeing, kayaking and spotting manatees. Just 7 minutes from the airport & 15 minutes from Sarasota, you’ll have access to beautiful beaches like Siesta Key & Anna Maria Island. Offering free WiFi, BBQ grill & firepit, this retreat is perfect for families seeking relaxation & adventure!

@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)

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.

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!

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

Blu Sky Cottage | Waterfront Home w/ Private Pool
Exclusive Amenities Include: • Private Heated Salt Water Pool & Spa • Waterfront Home w/ Unbeatable Views • Canal Access & Views • 1 Mile from Siesta Key Beach • 3 Bedrooms, 2 Full Baths • Covered Back Patio, Corn Hole, Ping Pong Table • 2 Kayaks & 2 Paddle Boards • Dog-Friendly with a Fee (2 small dogs up to 25lbs, not quoted in price & charged after approval)

Oceanfront home w/sunset views of Sarasota Bay
Treat your family, friends, and beloved small dogs 🐶 to an unforgettable oceanfront getaway ⛱️ in sunny ☀️ Florida! 🦅 🐬 🐠 🐚 🦀 Conveniently located near plenty of Sarasota's shopping and dining areas, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay. 🌴
Popular amenities for kayak rentals near Siesta Beach
House rentals with a kayak

The Shore House Private Dock Hot Tub

Modern 4bd | Heated Pool | Hot Tub + Studio Suite!

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

4B w/ Heated Pool | Walk to Siesta Key Beach!

1/2 Block from Beach- Private Boat Dock & 30' Pool

Edgewater Escape - 454

Waterfront Pool Home Steps to Beach

Peaceful home w/ pool - steps to Siesta Key Beach
Cottage rentals with a kayak

Waterfront Villa Delphina

Steps To The Beach, Private & Heated Pool, Renovat

Anna Maria Cottage w/Golf Cart

Serene Island Cottage Waterfront Haven

Cottage by the Bay - free charging, Level 2 EV

River Cottage 2/2 - Kayaks & Huge Deck-Old Florida

Sea Whisper: North End Gem w/ Pool & Boat Dock
Other vacation rentals with a kayak

Sun and Sea Gem on Siesta Key

Complete Privacy Mid Century 2mi to #1 Beach Pool

Waterfront Retreat | Heated Pool & Boat Dock

siesta breeze paradise suite

Gertrude's Siesta | Palm-view Pools Private-Beach!

Waterfront Wares Creek Cottage with dock access

siesta breeze suite

Siesta Key Direct Beachfront incl kayaks & SUPs
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 $167 CAD per night before taxes and fees

Verified guest reviews
Over 2,870 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
50 of Siesta Beach vacation rentals include wifi 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
- Pet-friendly 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
- Anna Maria Island Beach
- Raymond James Stadium
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Amalie Arena
- Caspersen Beach
- Tampa Convention Center
- Manasota Key Beach
- Vinoy Park
- Crescent Beach
- John's Pass
- Fort De Soto Park
- Tropicana Field
- Englewood Beach
- Cortez Beach
- Anna Maria Public Beach
- Img Academy
- River Strand Golf and Country Club
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park
- Jannus Live





