Waterfront vacation rentals in Holmes Beach

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Holmes Beach

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Anna Maria

4.94 out of 5 average rating, 155 reviews

Private 30' Pool and Boat Dock - Rated best on AMI

* 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. * There's no better way to unwind and forget all your troubles than staying at Sunshine Cottage, located in the City of Anna Maria!

Superhost

Rental unit in Bradenton Beach

4.84 out of 5 average rating, 179 reviews

"Dream Away" at The Beach Dreams Resort

Dream-away is the top right unit with one bedroom, one bath, full kitchen, washer/dryer, dish washer and a balcony facing Gulf Drive. This unit has a wonderful beach front view. The balcony is not on the Gulf Side. If you are interested in renting beach chairs, umbrella and a golf cart, please let us know. Two chairs and one umbrella are 25/day. We will drop off and pick up. Golf Cart can be rented for the day or the week. One small to mid size car is allowed on premises. Ask about larger cars.

Guest favorite

Rental unit in Holmes Beach

5 out of 5 average rating, 19 reviews

Luxury 2BD Oceanfront Condo + Private Parking

Unwind in this beachfront retreat! Just steps from the sand, this modern condo boasts stunning ocean views. Relax on the cozy turf patio with smart TVs & High-Speed WiFi. It comes with a fully equipped kitchen, & 2 private parking spots. Unique touches: The robot vacuum keeps things clean. Enjoy the Insta-worthy grass wall & a touch of nature on the cozy turf patio. 2 comfy queen beds ensure a good night's sleep. Location: Next to AMI trolley stop for island exploring! Dining, gym nearby.

Guest favorite

Condo in Longboat Key

4.93 out of 5 average rating, 147 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Guest favorite

Condo in Holmes Beach

4.88 out of 5 average rating, 43 reviews

Beach Haven #204

Beach Haven #204 at Seaside Beach House is favorite for guests of Holmes Beach and Anna Maria Island. This 1050 sq ft. One Bedroom, One Bathroom, on the beach condo is a welcome haven from the busyness of life. Whether you prefer relaxing by the pool or to walk 20 feet onto the white sands, this condo offers an escape from the world. With a Kingsize Bed and a Queen Sofa sleeper this a perfect family getaway. Enjoy your morning coffee and evening watching the sunset on the balcony.

Guest favorite

Condo in Bradenton Beach

4.91 out of 5 average rating, 137 reviews

Beachfront condo in paradise

Relax, you made it, you’re at the beach now. No fighting traffic for 90 minutes to get over the drawbridge to Anna Maria Island and driving around looking for a spot to park. You only have to go down 14 stairs from this second floor condo to have your toes in the powder soft sand. Enjoy the sunset from your balcony as it sinks into the Gulf. Perfect for a romantic couple getaway whether it be an anniversary, birthday, or some overdue R&R. Or bring the kids for a fun stay at the beach.

Guest favorite

Condo in Holmes Beach

4.87 out of 5 average rating, 63 reviews

Beachfront 1BR with pool

This 1 bd/ 1 bath condo on the Gulf of Mexico is our little slice of paradise! Located on the second story in a small 8-unit complex, It is beautifully decorated and fully furnished, including a sofa pull out in the living room to accommodate *up to* four guests in the unit. The space includes a full kitchen with cookware and accessories. There are many shops and restaurants within walking distance, as well as access to the free Island trolly to take you wherever you may need to go!

Guest favorite

Guesthouse in Bradenton Beach

5 out of 5 average rating, 129 reviews

Bradenton Beach Sunsets 1, 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.

Guest favorite

Condo in Bradenton

4.98 out of 5 average rating, 151 reviews

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

Guest favorite

Home in Bradenton

4.99 out of 5 average rating, 132 reviews

My Peaceful place on the bay.

Tucked away from the hustle and bustle, my mobile home is located in a very unique neighborhood right on the bay with a little beach 2 min. down the road from my house, where you can sit and enjoy the views or fish. The homes are a combination of mobile homes like mine and houses with the most wonderful people of all walks of life. Very quiet, friendly and 5 min. to Bradenton beach and 10 min. to AMI.

Guest favorite

Condo in Longboat Key

4.8 out of 5 average rating, 215 reviews

SRQ/Longboat Key Beach - kid friendly/romantic B1

Beachfront on beautiful Longboat Key, this condominium, unit 234, offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air.

Guest favorite

Rental unit in Holmes Beach

5 out of 5 average rating, 18 reviews

Beach Views! Pool & Pickleball! Kid Friendly!

Whether you're seeking relaxation or adventure, this Airbnb listing offers it all. So come, unwind, and experience the beauty of the beach, the convenience of nearby restaurants and shops, and the luxury of beachfront living in a dreamlike setting. Your beach vacation of a lifetime awaits! Book now to secure your slice of paradise. at this peaceful place to stay.