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

Cypress Lakes Barn Retreat
Rest & relax at this newly constructed barn loft apartment, located on a 4 acre hobby farm in Odessa, Florida on a private lake. This one bedroom, one bath and kitchen is clean, fun, and convenient. We have 2 daily feedings of farm animals at which you can participate including horses, cows, goats, & chickens; or you can choose to kayak on the lake. This memorable place is anything but ordinary, and is conveniently located 11 miles from the airport and is a quick drive to dining & shopping.

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.

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.

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.

Waterfront Pool Oasis •Kayak, Games & Sunset Views
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

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 awaits—book 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 kayak rentals in Anna Maria
House rentals with a kayak

Kayak + Canal-View | Next to Anna Maria & Reserve

CANAL Oasis Heated Pool-Hot Tub-Waterfront- Kayaks

Waterfront Manatee Home Pool, Dock, Optional Boat

Ocean Dreaming: Waterfront Home with Heated Pool,

Piece of paradise in Indian Rocks Beach.

Waterfront | Pet-Friendly | Near Beach/Downtown

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

Waterfront Key West Style Home
Cottage rentals with a kayak

Pink Gulfside Cottage, Steps to Beach, Pets OK

Anna Maria Cottage w/Golf Cart

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

New Country Cottage on Lake Manatee Lakewood Ranch

Cottage & Tree ~ by the Sea

2/2 Charming Riverfront Cottage w Deck & Kayaks

Happy Camper Cottage | Cozy Oasis with Hot Tub

Alafia River Cottage
Other holiday rentals with a kayak

[TRENDlNG] Modern 5BR Pool Villa + Arcade & Sauna

Private Dock~Covered Pool~Hot Tub~Game Room Fun!

Waterfront/Kayak with Manatees/Pool/Fish

Luxury Sport Vacation Pool House-Downtown Sarasota

Coastal Farmhouse & Pool

Waterfront Suite-20 min to Gulf Beaches

Coastal Haven w/pool in Bradenton

Tranquil Tide Villa - Waterview! 15 min to beach
When is the best time to visit Anna Maria?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 422 | € 583 | € 802 | € 814 | € 729 | € 757 | € 494 | € 386 | € 350 | € 239 | € 716 | € 684 |
| 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 € 156 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
30 of Anna Maria holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Anna Maria rentals

4.9 Average rating
Anna Maria stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a kayak Manatee County
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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