Vacation rentals with a kayak in Holmes Beach

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

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

Beach access + 2 min walk to Sand + Heated Pool!

🏝️Welcome to AMI Beachside Bungalow, a newly remodeled island getaway just a 2-minute walk from the soft white sands of one of the most private and picturesque stretches on Anna Maria Island. This street does not allow public parking for beach access, offering rare privacy and tranquility. ☀️Glowing with natural sunlight and designed for comfort, AMI Beachside Bungalow offers the perfect blend of coastal style and laid-back island living for multi-generational families. VRC# 21-000132

Sunshine Cottage: 30’ Pool & Dock, Steps to Beach

o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

Margaritaville Resort 3BR | Pool | Anna Maria

Welcome to Our Happy Place, a stylish 3BR/3BA condo in Margaritaville at One Particular Harbour, Harbour Isles. Enjoy two en suite baths, a fully stocked island kitchen, dining for six, and a screened lanai overlooking peaceful lake and preserve views. Designed by an interior decorator for a calm, coastal feel. Resort pool, splash pad, and grills on site; Holmes Beach is just 2 miles away. Dog-friendly, with a dedicated workspace for remote days. Sleeps 6 in real beds, no bunks.

Bay Breeze Cottages #2

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

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.

Bay beauty with heated pool, spa, games, ping pong

Stunning waterfront Anna Maria Island retreat perfect for families! Enjoy a private heated saltwater pool, hot tub, and boat dock just steps from the Gulf beaches. This 3-bedroom home comfortably sleeps your group and offers an oasis with kayaks and paddle boards included. Wake up to beautiful bay sunrises in this centrally located paradise. Please remember you are vacationing in a residential area. Noise ordinances at night are in place. Permit: VRC21-000104

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, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.

Main St Gem! Walk to shops, dining & beach!

Steps from beach access! Welcome to "Strawberry Sunset" at the Gulf Drive Inn -Where Sunsets are Sweeter! a spacious 1 bed/1 bath suite with a sofa bed, full kitchen & 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 a beachside stay, The Gulf Drive Inn has it all!

Las Palmas Beach Rentals unit 2

Ground floor; limited beach view . Steps to the white sandy beach. Free parking to registered guest. Furnished rooms, full size kitchen, linens provided. Free trolley stop on the block. GREAT LOCATION! Shopping and restaurants short walking distance. Check out our guidebook for additional island tips. Once booked it will be in your itinerary.