
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 - 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.

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.

Oasis at Little Harbor
Renovated Condo in beautiful Little Harbor Beachfront Resort located in Ruskin, Florida!! A complex full of amenities that you can enjoy during your stay. It has two heated pools and a Jacuzzi which you can use to relax while you vacation. There is also a playground, tennis and basketball courts, and an area for barbecues with tables and chairs to eat with an amazing view! Come and stay in paradise!!!

Waterfront Coastal Condo 2 Blocks to Beach
đ Ultimate Waterfront Escape â Adventure Awaits! đ´ââď¸đââď¸ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle in a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more. We are pet friendly! Pet fee is $150 per pet.

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.
Popular amenities for kayak rentals in Anna Maria
House rentals with a kayak

Hibernate in our Bear Creek Home

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

Waterfront Manatee Home Pool, Dock, Optional Boat

Summer House longboat key

Piece of paradise in Indian Rocks Beach.

Waterfront / Heated Pool / Pet + Boat Friendly

*New* Waterfront Retreat: Pool, Spa, Dock & Views

Winter Luxury Stay | Pool, Hot Tub & Firepit
Cottage rentals 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!

Cottage & Tree ~ by the Sea

2/2 Charming Riverfront Cottage w Deck & Kayaks

Alafia River Cottage

Steps To The Beach, Private & Heated Pool, Renovat
Other holiday rentals with a kayak

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

Gulf Beach Getaway-STEPS FROM BEACH

Waterfront/Kayak with Manatees/Pool/Fish

Pool, Bay View, 5 min St Pete Beach @ Sand Dollar

Waterfront Oasis

Waterfront Duplex- hot tub, bikes, kayaks, SUP

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

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 | ⏠414 | ⏠572 | ⏠787 | ⏠799 | ⏠715 | ⏠743 | ⏠661 | ⏠509 | ⏠462 | ⏠283 | ⏠702 | ⏠671 |
| 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 âŹÂ 153 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 â averaging 4.9 out of 5!
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- Rentals with a patio Anna Maria
- Bungalow rentals Anna Maria
- Rentals with a hot tub Anna Maria
- Rentals with a firepit Anna Maria
- Beachfront rentals Anna Maria
- Fitness-friendly rentals Anna Maria
- Pet-friendly rentals Anna Maria
- Cottage rentals Anna Maria
- Family-friendly rentals Anna Maria
- Apartment rentals Anna Maria
- Luxury rentals Anna Maria
- Rentals with a washing machine and dryer Anna Maria
- Rentals with beach access Anna Maria
- Rentals with lake access Anna Maria
- Flat rentals Anna Maria
- Rentals with a kayak Manatee County
- Rentals with a kayak Florida
- Rentals with a kayak United States
- 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




