Beachfront holiday rentals in Anna Maria

Apartment in Bradenton Beach

4.91 out of 5 average rating, 177 reviews

Beachfront condo in paradise, Anna Maria Island

You only have to go down 14 stairs from your second-floor beachfront condo to have your toes in the powder soft sand. A queen size bed with a soft mattress in the bedroom and a queen size pullout couch in the living room. Full kitchen in the unit and laundry available downstairs. Cable and high speed internet included. One assigned parking spot. Enjoy the sunset from your balcony as it sinks into the Gulf. Perfect for a romantic couple getaway or bring the kids for a fun stay at the beach

Superhost

5 out of 5 average rating, 3 reviews

Sea La Vie by Duncan Real Estate

Welcome to Sea La Vie! This is the relaxing Island getaway that you have been looking for. You and the family will love staying in this beautiful three-bedroom, two-bath elevated home nestled in secluded surroundings, just one block north of Pine Avenue in the village of Anna Maria. It is common to see families riding bikes or Segways down the quiet neighborhoods. Walk the Boardway at sunrise, have breakfast at a local Cafe, or spend the day fishing on a Charter or at one of our 2 Piers.

4.98 out of 5 average rating, 46 reviews

Flat in Holmes Beach

Luxury 2BD Oceanfront Condo + Private Parking

🏡 Modern Condo with Stunning Ocean Views: - Cozy turf patio - Smart TVs & high-speed WiFi - Fully equipped kitchen for easy meals - 2 private parking spots for hassle-free stays - 2-minute walk to the beach ✨ Unique Features: - Robot vacuum keeps things tidy - Insta-worthy grass wall adds charm - 2 comfy queen beds for a restful sleep - Queen-sized inflatable extra bed 📍 Prime Location: - Next to the AMI trolley stop for island exploring - Walking distance to dining, gym & more!

5 out of 5 average rating, 12 reviews

Home in Holmes Beach

Oceanside Retreat-Rest & Recover-Hot Tub-Hammock

Whether escaping the cold winter days, or wanting to unwind from all the stress, Solace West is the perfect place for you. Walking distance to Anna Maria's beautiful beaches, restaurants, shops and more. The hot tub is set to 104*. With its waterfall feature and lights it's waiting for you to step in and unwind those overworked muscles. Whether inside enjoying the beautiful tranquil decor or outside enjoying any of the many amenities, we believe you may never want to leave.

4.94 out of 5 average rating, 18 reviews

Ocean Air Oasis-New Centrally Located AMI Luxury

Immerse yourself in coastal luxury at this exceptional 3-bedroom, 2.5-bathroom custom home, where opulent high-end finishes and stunning pecky cypress floors adorn every nook. Revel in the impeccable features, including Sub-Zero and Wolf appliances, marble countertops, Shaw’s sinks, and exquisite custom woodworking, all bathed in abundant natural light. This delightful space offers panoramic views of the lavish backyard, complete with a heated pool and spa.

Cottage in Bradenton Beach

4.98 out of 5 average rating, 178 reviews

Bradenton Beach Sunsets 2, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

4.94 out of 5 average rating, 106 reviews

Home in Holmes Beach

The Peachy Beach House, steps to the gulf

Hurricane season cancellation possible. Saturday-Saturday for check-in and out. Two bedroom, 2 full bathroom, new heated private pool Steps from semi-private gulf beach, this 3 story on a quiet street in N. HB Well-stocked kitchen, 2 TVs, large master which is more like resort suite with new tempurpedic king bed Gulf views from bedrooms. You’ll find: crib, high chair, beach chairs, wagon, canopy, beach toys and towels!

5 out of 5 average rating, 12 reviews

Home in Holmes Beach

L'Oasis West w/Dip Pool

Completely remodeled, this beautifully 2-bedroom duplex, crafted to enhance your living experience. Every detail has been thoughtfully designed to create a serene and inviting atmosphere. New images showcase this stunning transformation, come visit us to see the beauty in person! Additionally, West and East are now available for rent together, featuring convenient adjoining doors through the utility room.

Guest house in Anna Maria

5 out of 5 average rating, 31 reviews

The Boathouse

Would you like to feel like you are sleeping in a tree house with all the luxuries and comfort of a high end hotel? Then welcome to our brand new guest house, which accommodates a maximum of two guests and is a completely private tropical oasis. Standing on the edge of Lake LaVista, surrounded by tropical palms where you have use of the private and beautiful pool which we heat during the winter months.

5 out of 5 average rating, 7 reviews

Sea Shack - 2bd/2ba POOL Home

Welcome to Sea Shack, an inviting ground level vacation home with a pool just steps away from the beach! Visit Pine Ave’s locally-owned boutiques and restaurants just a five-minute walk away. This rental accommodates up to 6 guest. Fully equipped kitchen has plenty of storage space for all your cooking necessities. Baby accessories available for rent: Snoo bassinet High chair Pack and play

Superhost

5 out of 5 average rating, 6 reviews

The Shell House

Adorable 2 bedroom, 2 bath beach cottage with private, heated pool. Located on the north end of the island and only 3 houses from the beautiful white sand beach of Anna Maria Island. Relax and unwind in the spacious pool, surrounded by tropical palms. The cottage has a large covered and screened patio in the backyard by the pool.