
Holiday rentals with a kayak in Anna Maria
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Anna Maria
Guests agree: these holiday homes with a kayak 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.

salt living at its best
- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65ā 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 Peteās, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

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.

Waterfront tiny in St Petersburg - The āVā
The āVā is your perfect getaway to make fun memories. Note: You MUST have a 5 star rating on airbnb ! Take yourself back to the good old days of simplicity and relaxation. Paddle-board from your own private mangrove beach through the canals and to Tampa Bay. Experience dolphins swiming along side you, manatees feeding on sea grass or baby sharks out by the sandbar just 200 yards from the beach. The āVā rests in a culd-de-sac in a quiet waterfront neighborhood just 10 minutes south of DT.

Bay Lake Cottage
Youāll 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 TVās, 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.

Hibernate in our Bear Creek Home
This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

River House with Kayaks. Relax on the River.
Grab a kayak, and hop on the river for a chance to see some of Florida's wildlife. Birds, otters, and alligators! The Riverhouse is a one of a kind vacation home. A fully equipped kitchen, living Rm with leather couches and a dining area. 3 bdrms- a King in the Master, 2 twins in 2nd and a bunk rm, 2 full baths, a balcony, and 2 patios. Situated on a quiet cul-de-sac, only 5 mins from I-75 and 10 mins from UTC Mall, Benderson race park, and exceptional dining experiences.

Waterfront Gem/ Pool Spa+ Dock/ Near Bridge Street
Anna Maria Waterfront oasis! **5 min walk to beach, private dock, pool heat included!!** Relax in the private heated pool, sip coffee on the dock, or walk to the beach. This bright, updated home has spacious living areas, a stocked kitchen, smart TVs, fast Wi-Fi, and cozy beds. Great for families or couples! Grill by the pool, dine under the stars, or fish from the dock. Includes washer/dryer, beach gear, and parking. Your peaceful, sunny getaway awaitsābook now!

Florida Cracker Cabin on cattle ranch/Myakka River
We are located in Myakka City, FL, which is a short drive to Siesta Key and Lido Beach and Sarasota! Enjoy a peaceful stay in our newly built, unique, air-conditioned cracker cabin. The cabin sleeps 4 guests and is located in the middle of our 1,100 acre working cattle ranch. Step outside and you are right on the Myakka River and can sit by the fire-pit at night and enjoy the sounds of nature. While your visiting, enjoy a kayak down the Myakka River.

Discounted October Stays w/Private 30' Dock & 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.

Bayside Retreat your tropical oasis
"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

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.
Popular amenities for Anna Maria kayak rentals
Holiday House Rentals with a Kayak

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Oceanside 3BR with Private Pool & Boat Lift

CANAL Oasis Heated Pool-Hot Tub-Waterfront- Kayaks

Waterfront Manatee Home Pool, Dock, Optional Boat

Summer House longboat key

Cozy Coastal Getaway

Piece of paradise in Indian Rocks Beach.

King Bed/Pool/Game Room/Fire Pit/Hammock/Near AMI
Cottages with a kayak

Pink Gulfside Cottage, Steps to Beach, Pets OK

Anna Maria Cottage w/Golf Cart

Lido Key Beach Bungalow with Private Heated Pool!

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

Cottage & Tree ~ by the Sea

New Country Cottage on Lake Manatee Lakewood Ranch

2/2 Charming Riverfront Cottage w Deck & Kayaks

Alafia River Cottage
Other holiday rentals with a kayak

Stylish Beachfront Condo, Stunning Views

Waterfront/Kayak with Manatees/Pool/Fish

Resort-Style Ground Floor Suite Heated Pool/Spa

The little house!

Waterfront Suite-20 min to Gulf Beaches

Coastal Haven w/pool in Bradenton

Sea Gem | Waterfront Oasis w/ Pool, Dock + Kayaks

Seas The Day By The Bay
When is the best time to visit Anna Maria?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $749Ā AUD | $1,036Ā AUD | $1,426Ā AUD | $1,446Ā AUD | $1,295Ā AUD | $1,346Ā AUD | $1,197Ā AUD | $922Ā AUD | $837Ā AUD | $512Ā AUD | $1,272Ā AUD | $1,215Ā AUD |
| 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 holiday rentals with a kayak in Anna Maria

Total holiday rentals
Explore 30 holiday rentals in Anna Maria

Nightly prices starting at
Anna Maria holiday rentals start at $278Ā AUD per night before taxes and fees

Verified guest reviews
Over 1,010 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Anna Maria holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Anna Maria rentals

4.9 Average rating
Anna Maria stays are highly rated by guestsāaveraging 4.9 out of 5!
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- John's Pass
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Dunedin Beach
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Cortez Beach
- Anna Maria Public Beach
- Lido Key Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- ZooTampa at Lowry Park
- North Beach
- Manasota Key Beach
- River Strand Golf and Country Club
- Adventure Island
- Tampa Palms Golf & Country Club