Waterfront vacation rentals in Anna Maria Island

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Top-rated waterfront accommodations in Anna Maria Island

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

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Guest favourite

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.

Sep. 3 – 10

$260 CAD per night

Guest favourite

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!

Nov. 6 – 13

$828 CAD per night

Guest favourite

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).

Jul. 19 – 26

$181 CAD per night

Guest favourite

Cottage in Bradenton

4.94 out of 5 average rating, 301 reviews

Historic Private King Bed Suite-Near Beach-D’Town.

Your relaxing vacation is here! Private Cottage with a huge deck. Wonderfully furnished with plush linens, beach towels/chairs. A great nights sleep with a king-size bed and pull-out couch which serves as 2nd bed. Private kitchen and bath. TV and fast WIFI. We are located in a historic and quiet neighborhood in DT Bradenton. There are 3 villas on our large corner property. Off street parking. Quiet times are between 10PM until 7:30AM. Please respect others. Walk to many great restaurants!

Jul. 13 – 20

$187 CAD per night

Guest favourite

Condo in Longboat Key

4.93 out of 5 average rating, 144 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.

Sep. 5 – 12

$471 CAD per night

Guest favourite

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.

Nov. 13 – 20

$211 CAD per night

Guest favourite

Condo in Longboat Key

4.97 out of 5 average rating, 148 reviews

Charming Condo on the Coast!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with complimentary chairs and umbrellas. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Oct. 24 – 31

$510 CAD per night

Guest favourite

Condo in Indian Rocks Beach

4.79 out of 5 average rating, 225 reviews

Waterfront Condo w/ Boat dock, 2 min walk to beach

This cozy one bedroom, one bath condo is only 2 blocks from the beach with family-friendly activities, nightlife, and public transportation nearby. The place is perfect for solo travelers, couples, & even small families who looking to have a relaxing time. Located right on the intercostal waterway. You can enjoy your coffee on the dock while watching the sunrise. Also, a great spot for seeing dolphins. Shops, food , and entertainment are all located within walking distance. BTR #266

Sep. 15 – 22

$203 CAD per night

Guest favourite

Condo in Indian Shores

4.96 out of 5 average rating, 143 reviews

1 BR direct beachfront! Now avail. 8/29-9/11.

Our condo is directly on the beach!! It is close to restaurants and dining, mini-golf, Clearwater and St. Pete's Beach. About 25 miles from Tampa, Florida for the Buccaneers NFL football and Lightning NHL hockey! We are about 37 miles from Busch Gardens. Only 95 miles to Disney World in Orlando! Mini-golf right across the street! You’ll love my place because of the neighborhood. My place is good for couples, small families, solo adventurers, and business travelers.

Dec. 4 – 11

$255 CAD per night

Guest favourite

Apartment in Madeira Beach

4.85 out of 5 average rating, 337 reviews

B⎈AT HOUSE OASIS⚓Steps to the water⚓Walk to Beach!

Wake up just feet from the water, and hear the Sea Gulls at the freshly renovated Boat House! Behind Johns Pass village, this stand alone apartment (NOT A BOAT) canal view, filled with boats, and frequent visits from dolphin! Shops, restaurants, nightlife and the beach, all just a short walk from you! 100 yard walk to Johns Pass, stroll the board walk, grab some ice cream and take a short walk to the beach!*Queen bed*fast wifi*Smart TV*Waterfront docks and view!

Nov. 16 – 23

$183 CAD per night

Guest favourite

Condo in Holmes Beach

4.96 out of 5 average rating, 116 reviews

Beautiful beachfront condo for perfect vacation

Beautiful, cozy, elegantly furnished, spacious (1350 sqf with a large terrace), beachfront, 2 bedroom - 2 bathroom condominium, in the best managed, boutique-style gulf front residential complex on Anna Maria Island in Florida for an ideal vacation. Heated pool and hot tub, 2 tennis courts, 2 elevators, top floor unit, high speed internet, washer/dryer in unit, beach chairs, close to supermarket (Publix) and restaurants, free island trolley, rich cultural life.

Jul. 20 – 27

$422 CAD per night

Guest favourite

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. 15 – 22

$325 CAD per night