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, 279 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.

Sep 18 – 25

R2,638 ZAR per night

Guest favorite

Home in Anna Maria

4.93 out of 5 average rating, 153 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 1 – 8

R10,049 ZAR 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).

Aug 23 – 30

R1,775 ZAR per night

Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 13 reviews

Lamantin- 2 bed/2bath North End, beach 2 min walk

Welcome to the Lamantin, duplex on the North End of Anna Maria directly across from the beach with direct beach access 2 properties away. Relax at this updated 2 bed/2 bath tropical unit that has everything you could ask for. Rent one unit or both. Perfect for a group of extended family and friends. The master features a queen-size bed and ensuite bathroom. The second bedroom has a king-size bed. The updated kitchen is equipped with all the basics, including pots/pans to make a delicious meal.

Jan 7 – 14

R8,915 ZAR per night

Guest favorite

Apartment in Ruskin

4.85 out of 5 average rating, 104 reviews

Sunset Del Mar (Studio with view of Tampa Bay)

Living the Florida lifestyle right on beautiful Tampa Bay. The Inn at Little Harbor is a secluded resort style community offering waterfront accomodations with amenities that include 2 heated pools, jacuzzi, tennis courts, a beautiful sandy beach, 2 full service restaurants/bars with live music,kayak and paddle board rentals, jet ski rentals, boat rentals and fishing charters and some of the most beautiful sunsets you have ever seen. Amenities are within walking distance from your doorstep.

Aug 3 – 10

R2,061 ZAR per night

Guest favorite

Apartment in Anna Maria

5.0 out of 5 average rating, 9 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.

Oct 9 – 16

R3,922 ZAR per night

Guest favorite

Condo in Bradenton Beach

4.91 out of 5 average rating, 131 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.

Mar 29 – Apr 5

R10,046 ZAR per night

Guest favorite

Condo in Bradenton

5.0 out of 5 average rating, 57 reviews

Canal Facing Private Condo + 5 mins to Anna Maria

Looking for a relaxing getaway in paradise? Look no further than this newly renovated charming 1 bedroom canal front retreat, just 5 minutes from the pristine beaches of Anna Maria Island. Enjoy close proximity to the beach, a fully equipped kitchen, and a comfortable living area. Nearby attractions include white sand beaches, restaurants, and shops. Return to your peaceful oasis and unwind in the quiet serenity of the canal front location. Book now for the ultimate Florida vacation!

May 31 – Jun 7

R2,222 ZAR per night

Guest favorite

Condo in Tampa

4.94 out of 5 average rating, 218 reviews

Modern Waterfront Condo - Captivating Sunset Views

This waterfront one bedroom condo will be your perfect place to relax and make new beautiful memories whether is for holiday or business. It has a fully equipped kitchen. Guests will have full access to the resort where they can enjoy the side pool bar, heated pool, fire pit, coin operated laundry and dryers. Located near Tampa airport (TPA). Within walking distance of public beach restaurants, and Courtney Campbell trail. Resort doesn't have access to the beach.

Aug 19 – 26

R2,425 ZAR per night

Guest favorite

Guesthouse in Bradenton Beach

5.0 out of 5 average rating, 123 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.

Nov 19 – 26

R3,910 ZAR per night

Guest favorite

Home in Bradenton

4.98 out of 5 average rating, 198 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.

Jun 15 – 22

R2,337 ZAR 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 1 – 8

R6,497 ZAR per night