Waterfront vacation rentals in Anna Maria

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Top-rated waterfront rentals in Anna Maria

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

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Guest favorite

Apartment in Treasure Island

4.91 out of 5 average rating, 278 reviews

Attractive Beachfront Studio - Live Like a Local!

The true treasure of Treasure Island! Tucked right off of Gulf Blvd, on a secluded beach, this comfortable newly remodeled private studio is nestled on a lushly landscaped beachfront residential property with renters on-site. This cozy spot is all about barefoot luxury — you're just steps from the beach and biking or walking distance to laid back beach bars, live music & restaurants. Please note: There’s no guest parking available, but paid parking is nearby as well as a frequent public trolley.

Oct 20 – 27

ﺩ.ﺇ520 per night

Guest favorite

Home in Anna Maria

4.93 out of 5 average rating, 152 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!

Dec 5 – 12

ﺩ.ﺇ1,952 per night

Guest favorite

Home in Bradenton

4.94 out of 5 average rating, 153 reviews

Peaceful Braden River Oasis: Cottage

Come get away to this river retreat just outside of Lakewood Ranch. This property has three separate rental units on it including this charming single bedroom cottage with access to the river. It comes with everything you need to enjoy a wonderful vacation! The other units on this property are the Guest House, a larger studio unit 1 bed/1 bath sleeps 2 (Search Peaceful Braden River Oasis: Guest House) and the Main House, a 2 bed/2 bath sleeps 7 (search Peaceful Braden River Oasis: Main House).

Jan 5 – 12

ﺩ.ﺇ414 per night

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

NEW 4 Day MAY opening Sarasota #1 Luxury Villa

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Dec 26 – Jan 2

ﺩ.ﺇ2,351 per night

Guest favorite

Apartment in Anna Maria

5.0 out of 5 average rating, 8 reviews

Canal front 1 BR on Pine Ave

This cute 1 Bedroom / 1 Bath efficiency is canal front and right in the heart of Pine Ave, on the North end of Anna Maria city. So many boutiques, stores, a small grocery store, ice cream shops and more along this very short 0.6 mile avenue!! Turn left and run into Tampa Bay and the Anna Maria City Pier or turn right and fall into the Gulf of Mexico. It is a very active area, including the Anna Maria Island Historical Society and the Old City Jail. 21 years or older- ID may be requested.

Jun 1 – 8

ﺩ.ﺇ724 per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

Oct 11 – 18

ﺩ.ﺇ481 per night

Guest favorite

Condo in Bradenton Beach

4.91 out of 5 average rating, 129 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.

Sep 9 – 16

ﺩ.ﺇ1,118 per night

Guest favorite

Home in Bradenton

5.0 out of 5 average rating, 7 reviews

Great Times & Tan Lines

Make memories in your gorgeous waterfront townhome with 2 bedrooms and 1 ½ baths. An intimate community with 20 units ideally located 3 miles from the laid-back beach life of Anna Maria Island or 4 miles from the energy of downtown Bradenton and Manatee Riverwalk. Walk to Palma Sola Causeway Park and boat ramp where you rent paddle boards, jet skis, kayaks, plus horseback riding in the water. Relax at home, fish off the dock or watch for visiting manatees and stingrays.

Aug 25 – Sep 1

ﺩ.ﺇ422 per night

Guest favorite

Guesthouse in Bradenton Beach

5.0 out of 5 average rating, 121 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.

Sep 10 – 17

ﺩ.ﺇ759 per night

Guest favorite

Home in Bradenton

4.98 out of 5 average rating, 197 reviews

My Sunny home on the Bay.

My Sunny Mobile Home is located within a 2 min. walk from the Palma Sola Bay right across from Anna Maria Island. Sit and enjoy the views on the little beach right on the bay. 5 min. drive to the most beautiful Gulf beaches. Watch the dolphins swim and relax on the beach. Snorkeling, fishing and great restaurants near by. Very quiet neighborhood with houses and mobile homes and close to everything for a relaxing vacation.

Jul 18 – 25

ﺩ.ﺇ543 per night

Superhost

Guesthouse in Anna Maria

5.0 out of 5 average rating, 3 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.

Dec 13 – 20

ﺩ.ﺇ1,262 per night

Guest favorite

Apartment in Bradenton Beach

4.88 out of 5 average rating, 204 reviews

Las Palmas Beach Rentals Unit 1

Upstairs unit with limited beach view across the street. Just a few steps to the white powder sand beach. 1 parking spot provided. This unit is for Max 3 persons. Hot tub downstairs. Spa just a few buildings to the south great massage and wellness center. We offer luggage drop off if you plan to uber/lyft and arrive before the check in time. Free trolley will give you service around the island.

Jan 23 – 30

ﺩ.ﺇ965 per night