
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.

Life's A Beach! Anyday arrival! Monthly discount!
Steps from beach access! Welcome to "Life's a Beach" at the Gulf Drive Inn - a spacious 1 bedroom/1 bathroom suite with a trundle, full kitchen and living area. This duplex style bungalow has resort-like amenities with a shared backyard space including a heated saltwater pool, spa and gas grill. Whether you're celebrating a birthday, anniversary, or simply in need of an extended beachside stay, The Gulf Drive Inn has it all! "Life's a Beach" is one of four resort suites at The Gulf Drive Inn.

salt living at its best
- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65â 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 Peteâs, 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.

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 itâs 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.

Waterfront Pool Oasis â˘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 â ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

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.

Sunset and beach view from your balcony Unit 403
A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

Holiday-January 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

Manatee Retreat B
Our newly renovated home sits on a beautiful canal and has access for kayaks, and other fun water activities. Sit on the patio or in the screened porch and watch the manatees play and the mullet jump. We are tucked away in our private oasis. It's only 206 steps to the beach. Easy walk to shops, bars and restaurants. Each bedroom has a queen bed, plus a pull-out couch in the living room for an additional bed.

Waterfront condo on top floor @ Boca Ciega Resort
Great view of water. Especially beautiful sunsets! Top floor end unit for privacy. Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking the intercoastal or stay indoors and enjoy puzzles and games.

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
Holiday House Rentals with a Kayak

Hibernate in our Bear Creek Home

Oceanfront w/ Pool, Dock & Boat Lift. Luxury 3BR

WTFR home heated pool, golf cart, kayaks, SUP

Waterfront Oasis

Waterfront Manatee Home Pool, Dock, Optional Boat

Summer House longboat key

Ocean Dreaming: Waterfront Home with Heated Pool,

Waterfront / Heated Pool / Pet + Boat Friendly
Cottages with a kayak

Sunny PaG Island rental w/bikes-just steps2beach

Pink Gulfside Cottage, Steps to Beach, Pets OK

Anna Maria Cottage w/Golf Cart

Lido Key Beach Bungalow with Private Heated Pool!

New Country Cottage on Lake Manatee Lakewood Ranch

Cottage & Tree ~ by the Sea

2/2 Charming Riverfront Cottage w Deck & Kayaks

Alafia River Cottage
Other holiday rentals with a kayak

Bayside Escape-Condo w/ Dock, Pool, and Near Beach

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

Resort-Style Ground Floor 1-Bdr., Heated Pool/Spa

Waterfront Duplex- hot tub, bikes, kayaks, SUP

AMI Dock of the Bay - "On the Water" 1st Floor

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

Pura Vida - Waterfront Home, kayaks, heated pool

Villa Al Golfo Tre Pristine Waterfront Oasis
When is the best time to visit Anna Maria?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $843 NZD | $1,165 NZD | $1,604 NZD | $1,626 NZD | $1,456 NZD | $1,513 NZD | $1,345 NZD | $1,037 NZD | $941 NZD | $576 NZD | $1,430 NZD | $1,366 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 $312Â NZD 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 guestsâaveraging 4.9 out of 5!
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
- Raymond James Stadium
- Turtle Beach
- Dunedin Beach
- Caspersen Beach
- Coquina Beach
- Vinoy Park
- Cortez Beach
- Lido Key Beach
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Manasota Key Beach
- Gulfport Beach Recreation Area
- North Beach
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Englewood Beach




