House holiday rentals in Anna Maria

4.95 out of 5 average rating, 104 reviews

Breezy Harbor AMI pool retreat near the Beach

Stunning Fall 2024 renovation done! Charming Breezy Harbor boasts a private heated pool and sits on a quaint corner of AMI. Upon arriving you will immediately feel stress melting away. You'll love grilling in the lush yard and a 6-min walk to the beach or the AMI trolley stop. A supermarket is a couple of streets over. The home is perfect for families, couples, 1-50Lb pet, and working remotely. Ample Parking for 2 vehicles and toys. *Ask us for shorter stays and always discuss your pets with us*

5 out of 5 average rating, 6 reviews

Casa Cay by Duncan Real Estate

Welcome to Casa Cay! This Bay front pool home on Anna Maria Island sounds like an absolute paradise! With its prime location on the North end between the 2 piers, stunning views of the bay and the Sunshine Skyway, and direct access to a private bay beach, it offers the quintessential island experience. The layout of the house, featuring three bedrooms and three bathrooms, including two suites with ensuite bathrooms, sounds perfect for families or groups of friends looking for comfort and ...

5 out of 5 average rating, 38 reviews

༄ Sunset Shore on Anna Maria Island ༄

Welcome to the perfect Anna Maria Island home on prestigious North Shore Drive. Overlooking a canal lake, Sunset Shore offers a serene escape just 2 blocks from the Gulf's legendary white sand beaches and steps away from Pine Ave's vibrant shops and restaurants. Explore the island easily with the nearby free AMI trolley, connecting you to the City Pier, all the way south on the island to Coquina Beach, and all attractions in between. It's a perfect blend of coastal relaxation and convenience!

4.9 out of 5 average rating, 59 reviews

Island in the Sun, luxury beach house,private pool

WELCOME to Island in the Sun ... this newly renovated home on AMI offers charm, comfort, and luxury. No damage from hurricane Helene or Milton. This Anna Maria Island vacation rental is located just one block south of Pine Ave and just a few flip flop steps away from the City Pier Bay Beach and the popular restaurant - The Waterfront. The City Pier Bay Beach offers narrow white sand beaches, views of the of the City Pier, the Skyway Bridge and the boats traveling back and forth in Anna ...

4.91 out of 5 average rating, 370 reviews

Home in Bradenton

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

Enjoy Florida sun in a stunning, newly renovated 4/2 pool home! We have provided almost everything we could think of including five 4k TVs w/ Netflix and cable, wifi, heated (optional) salt water pool w/ 7' privacy fencing, adult bikes, beach gear, Pack & Play, office, board games, relaxing lounge chairs, stocked kitchen, washer & dryer, garage parking, dog crate, all in a quiet and safe neighborhood. Oh, and of course it's just 5 miles to world renowned beaches.

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.

5 out of 5 average rating, 5 reviews

Kiwi Cottage~Private Heated Pool!~Shopping close!

2 bed 1 bath Coastal Beach Cottage! Interior has been completely remodeled and brand new furnishing! 5-minute walk to the beach • Private Heated Pool • Pet Friendly • Less than a 5-minute walk from Pine Ave shops and restaurants • Outdoor seating area/BBQ Grill Can be rented with Coconut Cottage for a larger number of people. Gate can be opened in the backyard, between Kiwi Cottage and Coconut Cottage, for an easy way to get between the 2 units!

4.94 out of 5 average rating, 178 reviews

Discount 33% June 3-Day and July 4-Day w/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.

4.94 out of 5 average rating, 107 reviews

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!

4.93 out of 5 average rating, 28 reviews

Luxury 3BD Beachfront Retreat with Heated Pool!

Step directly onto the sand from this luxury Gulf-front retreat in the heart of Holmes Beach. With a private heated pool, three king bedrooms—each with en suite baths—and high-end design throughout, Sandy Bottoms Beach House offers a rare combination of beachfront serenity and modern comfort. Relax on the private patio, take the trail to the beach, and enjoy a front-row seat to Florida’s most stunning sunsets.

5 out of 5 average rating, 12 reviews

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.