
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.

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 saltwater pool home - turf putting green
Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

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.

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

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach
Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

Tiny Oasis | Pool | Stocked Stay Near Indian Rocks
Welcome to The Tiny Oasis! A cozy boutique style retreat in Largo, FL, near Indian Rocks and Clearwater Beach that’s packed with luxury. Lounge by the plunge pool, fire up the Blackstone or enjoy an outdoor movie night. Unique touches and a 5-star experience prove that small spaces make big memories! Tap ‘Show More’ below! What’s There To Look Forward to? 👙Plunge Pool 🚿Outdoor Shower 🔴 Corn Hole ⛱️ Beach Gear 🍔Grill 🅿️ Private Parking 🍳Cook at Home 🧺 Your own private Washer/Dryer

@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)

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

Waterfront Duplex: 3 Blocks to Beach, Hot Tub, SUP
☀ Bay Views ☀ Shared Hot Tub ☀ Dock with Stand-up Paddle boards, Kayaks, Bikes ☀ Only 3 blocks to the sugary sands of Indian Rocks Beach ☀ Duplex- book independently or together ☀ Blackstone, 6 burner Charbroil Grill ☀ 10 Foot Custom Wood Bar w/ Jenga, Giant Connect 4, Corn Hole, Ringtoss ☀ Beach Wagons, Speaker, Zero Gravity beach chairs, beach towels, cooler ☀ Amazon Dot with Unlimited Amazon Music

2-night available 5/21 & 6/18-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.

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 Anna Maria kayak rentals
House rentals with a kayak

Canal-View Retreat • Kayak • Close to AMI

Cedar Sunsets-4 bed, 4 bath, 4 Houses to the beach

Mid-century cottage on Coffee Pot Bayou in Old NE

Manatee Retreat B

NEW Waterfront | Heated Pool | Kayaks

Large 3BR Home, Heated Pool! Close to Beach, IMG

Beach a la Mode | Luxury Anna Maria Island Home!

Shells and Shore Getaway
Cottage rentals with a kayak

Anna Maria Cottage w/Golf Cart

Lido Key Beach Bungalow with Private Heated Pool!

Steps2Beach-Walk everywhere-Bikes & gear Included

Little Manatee River Cottage

Cottage & Tree ~ by the Sea

2/2 Charming Riverfront Cottage w Deck & Kayaks

Sea Whisper: North End Gem w/ Pool & Boat Dock

Alafia River Cottage
Other vacation rentals with a kayak

Waterfront 5BR w/Pool, Spa, Boat Lift, Putting Grn

Next to Beach & Largest Pool on Island-258

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

Waterfront /Pool /Golf Cart /Pet + Boat Friendly!

Central location|Walk to beach, trolley & stores

Redington Beach near beach on ICW w/pool & dock

Tranquil Bay: Waterfront Home w/ Heated Pool

Family Fun Getaway | Pool, Hot Tub & Treehouse
When is the best time to visit Anna Maria?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$101,591 GYD | G$140,471 GYD | G$193,357 GYD | G$196,075 GYD | G$175,589 GYD | G$182,487 GYD | G$162,211 GYD | G$125,003 GYD | G$113,506 GYD | G$146,324 GYD | G$105,354 GYD | G$112,461 GYD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°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$60,620 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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- Rentals with a kayak Manatee County
- Rentals with a kayak Florida
- Rentals with a kayak United States
- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
- Turtle Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Caspersen Beach
- Amalie Arena
- Tiny House Siesta
- Dunedin Beach
- Bean Point Beach
- Cortez Beach
- Jannus Live
- Anna Maria Public Beach
- ZooTampa at Lowry Park
- Hard Rock Casino
- Tampa Palms Golf & Country Club
- Manasota Key Beach
- River Strand Golf and Country Club
- Tampa Convention Center




