Holiday rentals with a kayak near Anna Maria Island

3/3 condo with Pool - 2 miles to beach

Our Happy Place is a stylish 3-bedroom, 3-bath condo in the exclusive Margaritaville – One Particular Harbor at Harbour Isles. This spacious retreat features a fully stocked kitchen with island seating, a dining area for six, and a cozy living room that opens to a screened balcony with serene lake and nature views. Each bedroom offers comfort and privacy, with two en suite baths and thoughtful touches like remote-controlled ceiling fans and blinds. Guests can enjoy community amenities including

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

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.

Beach a la Mode | Luxury Anna Maria Island Home!

"Exclusive Amenities Include: • Private Heated Pool & Spa • Canal Front Access & Views • Private Rooftop w/ Incredible Water Views • 7 Minute Walk to Bayfront Park • Multiple Balcony Views w/ Loungers • 5 Bedrooms, 4.5 Baths • 2 King Beds, 2 Queen Beds & 4 Twin Beds (Sleeps 8) • Game Room • Poolside Dining Area • Outdoor Shower • Corn Hole & Ping Pong Table • Private 2 Car Garage • Free WiFi • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials"

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.

Ocean Dreaming: Waterfront Home with Heated Pool,

Waterfront home: pool, dock, golf cart, kayaks, paddle board. This home has a private, zero-entry heated pool and dock (tie up your own boat or daily/weekly rental). 6-seat golf cart, 2-paddle boards, 2-sea kayaks, 6-bicycles and more are included. Two master bedroom suites with water views and soaking tubs plus a third bedroom with custom King Bed and Twin bunk beds. Two living areas are also each furnished with a queen sofa sleeper to accommodate a total of 12 people.

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

Waterfront Retreat | Pool • Spa • Dock | Bridge St

🌴 Anna Maria Island Waterfront Oasis! Private dock + heated pool included. Relax by the pool, sip coffee on the dock, or walk just 5 minutes to the Gulf’s sugar-sand beach. Bright, updated home with stocked kitchen, fast Wi-Fi, smart TVs, and cozy beds—perfect for families or couples. Grill by the pool, dine outdoors, or fish from the dock. Boat/kayak friendly. Beach gear + parking included. Your peaceful island escape awaits.

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.

Castaway Cove - Short stays! AMI gem!

Relax with friends and family at Castaway Cove, a true piece of paradise located at the north end of Anna Maria Island near fabulous restaurants, boutiques, AMI city pier, and close to Bay and Gulf of Mexico beaches. Nicely appointed with three bedrooms and two bathrooms, this vacation home has a serene backyard with a private pool, hot tub, and plenty of entertainment space. Rental agreement to be signed before check in.

Sand Trap by Beach Boutique Rentals

*Features include* * Ultimate Bay front vacation home * Private heated pool and full Putt-putt course * Paddleboards, kayak * Gas grill and outdoor dining * Huge front porch with water view! * Elevated home (requires stairs) * 4 Bali inspired bedrooms and 4 bathrooms * Bay beach directly across the street with no houses between * Steps to Pine Avenue * Beach chairs, umbrella and cart * Dog-friendly!