Vacation rentals with a kayak in Anna Maria

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Anna Maria

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
A bright and airy living area features large windows allowing natural light to fill the space. Comfortable seating is arranged around a woven coffee table, with art pieces adorning the walls. A door leads to outdoor views, enhancing the inviting atmosphere.
Home in Terra Ceia
4.98 out of 5 average rating, 118 reviews

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.

Guest favorite
A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.
Home in Bradenton
4.97 out of 5 average rating, 115 reviews

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

Top guest favorite
A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.
Bungalow in Oldsmar
4.97 out of 5 average rating, 184 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Top guest favorite
The exterior of a waterfront home is shown, featuring a spacious lawn with palm trees and a paved driveway. A screened gazebo is visible nearby, and the calm water reflects the surrounding greenery and sky. The house has a light-colored facade, enhancing its inviting appearance.
Home in Riverview
4.97 out of 5 average rating, 170 reviews

Beautiful Waterfront Home on the Alafia River.

Beautiful Waterfront Single Family home on the Alafia River leading to Tampa Bay and the Gulf of Mexico. Bring your boats, jetskis, Kayaks, water toys, fishing rods, etc. Riverview Civic Center and Boat Ramp is literally a couple of blocks away from the property and trailer parking is available at the property. If it’s your lucky day, you will see manatees, dolphins, snook, redfish and stingrays right from the dock. Excellent fishing, restaurants and nightlife all on the river or by vehicle.

Guest favorite
Home in Longboat Key
4.86 out of 5 average rating, 139 reviews

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

Top guest favorite
Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.
Cottage in Tampa
4.98 out of 5 average rating, 260 reviews

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Top guest favorite
Home in Apollo Beach
4.95 out of 5 average rating, 158 reviews

Waterfront Pool Oasis Kayaks, Games & Beach Vibe

Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

Top guest favorite
A rustic tiny house stands within a lush garden, featuring a wooden deck adorned with comfortable seating. The entrance showcases large glass doors, framed by greenery, while a charming pathway of stones leads toward the entrance. Subtle decorative elements enhance the inviting outdoor space.
Tiny home in Ybor City Historic District
4.98 out of 5 average rating, 596 reviews

Cozy AF Tiny-House Oasis

Awarded a *Unique Stay* by Airbnb, welcome to the **Cozy AF Tiny-House Oasis**, a rustic tiny home that started its journey as a world-traveling storage container. Now transformed into a charming cottage, it’s filled with unique and fun details waiting to be discovered. Enjoy the entire backyard, complete with a hot tub, koi pond, fire pit, hammocks, greenhouse, and even a bunny garden! Our goal is not just to offer you a place to stay but an experience you’ll cherish forever

Top guest favorite
Condo in Sarasota
5 out of 5 average rating, 106 reviews

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

Whisk your favorite person away to BayDreaming! Retreat to this quiet 1BR/1.5BA condo, just an 8‑minute walk from Turtle Beach. Perfect for couples, it offers a private deck with canal and Gulf views, a heated pool for sunset swims, two supyaks, and a plush king bed for cozy nights. Enjoy garage parking, beach gear, and a peaceful community. Whether you’re here to relax or reconnect, this coastal retreat blends romance with Siesta Key serenity.

Top guest favorite
A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.
Home in Anna Maria
4.95 out of 5 average rating, 192 reviews

Limited Availably w/ Private Boat Dock & 30' 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.

Top guest favorite
An aerial view of a beachside home is presented, featuring a large porch facing the sandy shore. Colorful kayaks and a stand-up paddleboard are placed on the sand, while numerous lounge chairs are positioned along the beach, surrounded by clear turquoise waters.
Home in Anna Maria
4.96 out of 5 average rating, 100 reviews

ami skyview

When you open your door and step out, you will enjoy your own private white sandy beach, with sparkling blue/green, Gulf/Bay water. The location and view are incredible, only a blocks walk, to the famous Anna Maria City Pier, Pine Avenue, restaurants boutiques and shops. Enjoy kayaks, paddle boards and bicycles, all FREE, for our guests. Come and enjoy paradise! There is only one camera located at the front entrance (street side).

Top guest favorite
A private pool area is surrounded by lush greenery, featuring a spacious pool with a spa at one end. Sunlight reflects off the clear water, highlighting the relaxing atmosphere of the outdoor space.
Home in Sunset Park
4.91 out of 5 average rating, 153 reviews

Tampa Waterfront Heated Pool/ Hot Tub Oasis w Dock

Enjoy this South Tampa waterfront pool home, centrally located off Westshore. Close proximity to Clearwater, downtown Tampa, and Orlando. Featuring brand new contemporary finishes and breathtaking views. This home Is monitored on video surveillance on the exterior corners of the home as well as the back yard and front door ring camera. Device will record during reservations. No parties of any kind will be permitted.

Popular amenities for Anna Maria kayak rentals

When is the best time to visit Anna Maria?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$115,044 GYDG$177,264 GYDG$210,253 GYDG$195,846 GYDG$175,385 GYDG$182,275 GYDG$162,022 GYDG$124,857 GYDG$113,374 GYDG$146,154 GYDG$105,231 GYDG$112,330 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

Quick stats about vacation rentals with a kayak in Anna Maria

  • Total vacation rentals

    Explore 30 vacation rentals in Anna Maria

  • Nightly prices starting at

    Anna Maria vacation rentals start at G$60,550 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,280 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Anna Maria vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Anna Maria rentals

  • 4.8 Average rating

    Anna Maria stays are highly rated by guests—averaging 4.8 out of 5!

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