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.

Value · Location · Accuracy

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

Value · Outdoor spaces · Solo travel

Gulf Beach Getaway-STEPS FROM BEACH

This updated condo sits just 54 steps from the white sand of Holmes Beach. Experience dolphin sightings or sunsets from the rooftop balcony. Our renovated kitchen is fully stocked with all the amenities of home. Enjoy plenty of space with a large kitchen and living room and two private lanais. You’ll love this condo’s central location to all Anna Maria has to offer! *License CND5105468 *7 Night minimum stay *6 Occupants max *2 onsite parking spots *Noise curfew is from 10:00 p.m. to 7:00 a.m.

Location · Accuracy · Nearby

Casa Coquina AMI- Newly Renovated, steps to beach!

Newly renovated single family home , STEPS to the beach ( Direct beach access at the end of the street- 5 houses up from the beach) , private fenced in backyard with heated pool, hot tub & outdoor shower! Steps away from restaurants, bars and shops! 3 bedrooms and 2.5 baths Downstairs complete with a game room including a tv and ping pong table! *if you want to check in/out on any day other than a saturday please message me directly and i will see if the dates you request are available

Location · Outdoor spaces · Pool

Waterfront Home Private pool, elevator and dock

Luxury waterfront retreat w/pool, spa, boat ramp & dock! Elevator makes it perfect for multi‑generational family getaways. This brand-new home features airy open-concept living and 4 bedrooms (3 primary en-suites with King). Swim in the sparkling pool, soak in the spa, grill on the BBQ, and dine under the covered patio. Just minutes to Gulf beaches and local dining. Bring your boat and enjoy waterfront living from your own backyard oasis, where you can relax and watch manatees in the canal.

Location · Outdoor spaces · Grill

Canalfront Cottage Near the Beach!

Stars on the Water by AMI Locals Duplex in Holmes Beach, Florida VRC21-000115 Perfect for beach and bay lovers alike, Stars on the Water is a charming canal-front vacation home with a private dock, just a leisurely six-minute walk from Manatee Beach! This intimate two-bedroom, one-bath retreat offers stunning water views, a fully equipped kitchen, and a spacious outdoor patio with plenty of loungers and a BBQ grill, ideal for relaxing days in paradise. Located within walking, biking, or

Location · Outdoor spaces · Hospitality

New! Private + 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

Location · Comfort · Amenities

1/2 Block from Beach- Private Boat Dock & 30' Pool

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.

Value · Outdoor spaces · Accuracy

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.

Outdoor spaces · Location · Access

Bay Breeze Cottages #3

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.

Value · Location · Bathroom

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.

Outdoor spaces · Location · Kitchen

Beach Escape | Heated Pool | Walk to Beach & Golf

Escape to Beach Escape, a charming 3-bedroom, 3-bathroom Mediterranean-style house in the heart of Holmes Beach, Florida. Enjoy easy access to the pristine beach, walkable dining and shopping, and a free trolley stop. This home offers a private outdoor oasis with a heated pool, outdoor dining, and a gas grill. Explore the island with a complimentary golf cart and bikes. Experience the perfect blend of relaxation and adventure in this guest-friendly location.

Location · Getting around · Beach