
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.

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

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

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

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

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

Pergola Oasis | Walk to Beach + Outdoor Living
Welcome to Salty Palm, a newly remodeled coastal retreat in the heart of Holmes Beach. Just a short walk to the white sandy beaches of Anna Maria Island, this home features a private covered pergola with outdoor lounge seating and dining, creating the perfect space to relax day or night. Steps from shops and eateries, with nearby bike and golf cart rentals, plus access to community amenities including a boat ramp, kayak launch, fishing dock, and tennis & pickleball courts.

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.

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

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.

AMI Sunset Beach - Gulf View Retreat w/ Pool+Decks
AMI's Sunset Beach part of 7 miles of white sand beaches! • 200+ five-star ratings over all sites! • Gulf-views inside home. • Decks with views of Beach + Gulf + Pool. • Heated Pool with sun shelf. • Paddleboard + Kayak + Firepit + Patio + Grill. • High-speed WiFi. • Top floor of duplex. • Central location next to Sunset Beach.

Backyard Bliss Anna Maria Island
Welcome to Backyard Bliss, where resort-style living meets premier location! With the powdered sands of the Gulf of Mexico only 500 steps away and a retreat that offers endless amenities, a stay at Backyard Bliss will guarantee a smile on your face when you’re here, and a frown when you have to leave.
Popular amenities for Anna Maria kayak rentals
Holiday House Rentals with a Kayak

Heated saltwater pool home - turf putting green

Canal-front Sanctuary | Manatees, Pool, Hot Tub

Waterfront pool home w/dock, firepit, kayaks

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

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

4-Bed Coastal Retreat w/Ht Pool, Private, Near AMI

River House with Kayaks. Relax on the River.

Waterfront Mansion Sleeps 9 | Hot Tub & Kayaks!
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!

Little Manatee River Cottage

Steps2Beach-Walk everywhere-Bikes & gear Included

Cottage & Tree ~ by the Sea

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

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

Intercoastal 4 Bed 3 Bath Pool Home Mins to Beach

Billy's Beach Bungalow

Bay View Condo Isla Del Sol–Stunning Renovation

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

Family Fun Saltwater Heated Pool, Games, Peloton

Pool and Beach Side Full Remodel-166

Perfect Beach View Large 2 bedroom

Bay Breeze Cottages #1 (The Mahi-Mahi)
When is the best time to visit Anna Maria?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $921 NZD | $1,420 NZD | $1,684 NZD | $1,569 NZD | $1,405 NZD | $1,460 NZD | $1,298 NZD | $1,000 NZD | $908 NZD | $1,171 NZD | $843 NZD | $900 NZD |
| 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 $485 NZD per night before taxes and fees

Verified guest reviews
Over 1,280 verified reviews to help you choose

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

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday 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 holiday 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
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- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
- Anna Maria Island Beach
- Bean Point Beach
- Coquina Beach
- Lido Key Beach
- Turtle Beach
- Amalie Arena
- Vinoy Park
- Caspersen Beach
- Tampa Convention Center
- Dunedin Beach
- Sand Key Beach
- Cortez Beach
- Hard Rock Casino
- Manasota Key Beach
- St Pete Beach
- Anna Maria Public Beach
- Englewood Beach
- Jannus Live





