Waterfront vacation rentals near Anna Maria Island

4.95 out of 5 average rating, 146 reviews

A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.

Condo in Siesta Key

NO Stairs, Siesta beachfront. Walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.

4.98 out of 5 average rating, 252 reviews

Island Time!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! 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 secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

The backyard features a saltwater pool surrounded by artificial turf, creating a refreshing oasis. Sunlight brightens the outdoor space, accentuated by lush tropical landscaping. The elevated home showcases multiple balconies, while palm trees lend to the coastal atmosphere of the property.

4.97 out of 5 average rating, 35 reviews

Bayfront Beach access with Heated Pool!

Our modern yet beachy retreat is the perfect oasis on the North end of Anna Maria Island w/breathtaking panoramic views of Tampa Bay & the iconic Skyway Bridge. The backyard oasis features a refreshing saltwater pool & fully fenced backyard, complete w/artificial turf & outdoor shower. Just steps away, you'll find full access to a stunning white sandy beach & the crystal-clear waters of Tampa Bay! Conveniences have been carefully considered, creating the most ideal vacation destination!

4.98 out of 5 average rating, 185 reviews

A spacious living area features a light-colored sofa against a vibrant tropical leaf mural. A sleek white entertainment unit holds a flat-screen TV, complemented by a decorative lamp and a colorful area rug underfoot. Natural light filters through window blinds.

Condo in Bradenton

KING Bed + AMI Beaches + Beach Gear!

🎙️🦩Welcome to the Retro Flamingo! Your tropical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this retro “Old Florida” themed condo!

Condo in Pass-a-Grille Beach

Two beach chairs are placed under a large white umbrella on the pristine white sand. The tranquil blue water of the ocean is visible in the background, complemented by clear skies and palm fronds gently swaying in the breeze.

4.99 out of 5 average rating, 177 reviews

Beachfront in Pass-A-Grille w/ 2 bikes

Enjoy an intimate and relaxing stay on the best stretch of the St. Pete Beach of Pass-a-Grille. Walk out your door to the white sand towards the famous Don Cesar or dine on your deck facing the water. Free parking, 2 bikes, SUP board, towels, umbrella, beach chairs, & cooler! We are allowed 3 rentals under 28 yearly. Please inquire to see if you are one of the lucky guests to come. We love long term guests but understand not everyone can do this and simply need a little escape! 🤍

4.98 out of 5 average rating, 125 reviews

Home in Bradenton Beach

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.

4.95 out of 5 average rating, 207 reviews

Sunshine Cottage: 30’ Pool & Dock, Steps to Beach

o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

Apartment in Bradenton Beach

4.92 out of 5 average rating, 154 reviews

Newly Remodeled Beachfront Studio - On the sand!

ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

4.98 out of 5 average rating, 108 reviews

Beach Condo with Quiet, Private Beach

Escape to our serene 2-BR beachfront condo on Longboat Key. This corner unit offers stunning Gulf of Mexico views and sleeps 6. Enjoy direct beach access, a heated pool, and a private patio perfect for sunsets. Located in the quiet Beach Castle Resort, it's the ideal beach vacation rental for families or couples seeking a tranquil getaway. Walk to local restaurants and cafes from your peaceful retreat. A guest-loved home, consistently rated top 5% among Airbnb’s homes.

4.98 out of 5 average rating, 118 reviews

An outdoor pool area is surrounded by tropical landscaping, featuring palm trees and rocky formations. Comfortable lounge chairs are positioned near the pool, which is complemented by a shaded umbrella. Colorful beach balls add a playful touch amid the scenic water view.

Home in St. Petersburg

Sea Vue -King Beds | Stunning Views | 2MI to Beach

Welcome to Sea Vue, a luxury Western facing home offering unparalleled water views, superior outdoor living, 5 bedrooms with dreamy hotel style bedding and activities for the entire group. Located just 2 miles to award winning St. Pete Beach & a short drive to the booming Downtown area this home is sure to exceed guest's highest expectations. Prepare to experience the highest level of customer service and indulge in your own private oasis inside and out.

4.99 out of 5 average rating, 155 reviews

A bright kitchen is showcased, featuring modern cabinetry and appliances. A small dining area with two wooden stools is positioned next to a white countertop. Natural light fills the space through a nearby door and window, creating an open atmosphere.

Home in Cortez

Tranquility 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, very safe and friendly. 5 min. to Bradenton beach and 10 min. to AMI.

4.98 out of 5 average rating, 127 reviews

Home in Sarasota

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

Popular amenities for waterfront rentals near Anna Maria Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.97 out of 5 average rating, 469 reviews

A serene view of the Manatee River showcases calm waters reflecting the sky. Lush greenery surrounds the area, accompanied by a covered dock nearby. An American flag flutters gently, and a hint of a charming structure with a porch is visible to the right.

Apartment in Ellenton

Serenity on the Manatee

Apartment in Indian Shores

A spacious living area is furnished with two comfortable leather sofas and a wooden side table. A large flat-screen TV is positioned nearby. Natural light floods the room through expansive glass doors leading to a balcony, with ocean views visible in the distance.

4.92 out of 5 average rating, 226 reviews

Direct Beachfront Condo, Ocean balcony view!

Apartment in Longboat Key

Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.

4.96 out of 5 average rating, 124 reviews

Longboat Key-OCEAN FRONT- on the beach

Apartment in Treasure Island

An inviting living area features a light gray sofa and a round white coffee table. Large glass doors open to a private balcony with unobstructed views of the Gulf of Mexico, creating a seamless connection with the beachfront landscape.

4.94 out of 5 average rating, 191 reviews

Beachfront Condo w/ Ocean View - Newly Renovated!

Apartment in Indian Rocks Beach

A shared hot tub overlooks the water, with two guests enjoying beverages while gazing at scenic views. Lush greenery frames the scene, and a variety of kayaks and paddleboards are visible in the background, enhancing the outdoor atmosphere.

5.0 out of 5 average rating, 113 reviews

Waterfront Escape | Hot Tub • Kayaks • Beach 5 Min

4.97 out of 5 average rating, 155 reviews

A spacious living room features a large grey sectional sofa with teal accent pillows, a wooden coffee table, and a light blue area rug. Large glass doors provide access to an outdoor area, while a vibrant seascape painting adorns the wall.

Apartment in Bradenton

Sweet Retreat at Shorewalk!

4.94 out of 5 average rating, 142 reviews

Apartment in Siesta Key

Siesta Premier Location - The 'Calm of Siesta'

Apartment in Indian Rocks Beach

4.88 out of 5 average rating, 111 reviews

On private beach! Ground Level Full Kitchen Unit 6

Waterfront house rentals

4.96 out of 5 average rating, 149 reviews

A spacious patio is highlighted by a heated pool, surrounded by a decorative stone border. Comfortable outdoor seating is arranged nearby, beneath string lights that create a soft glow. A serene water view and lush greenery are visible in the background, enhancing the outdoor ambiance.

Home in Bradenton

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

4.98 out of 5 average rating, 122 reviews

A bright and airy living area features large windows allowing natural light to fill the space. Comfortable seating is arranged around a woven coffee table, with art pieces adorning the walls. A door leads to outdoor views, enhancing the inviting atmosphere.

Home in Terra Ceia

Private Island Old FL Waterfront Heaven on Earth

The exterior of a charming two-story beach house features a vibrant color scheme with light blue and white accents. Adjoining palm trees provide shade, while a spacious porch with outdoor seating offers a welcoming view of the surrounding yard. A sandy area leads to the driveway.

4.94 out of 5 average rating, 108 reviews

2nd House from the Beach with No Roads to Cross

5.0 out of 5 average rating, 65 reviews

Home in Holmes Beach

Waterfront, Heated Pool, Elevator, Fire Pit, Dock

4.96 out of 5 average rating, 77 reviews

Renovated 2bed /2 bath North End, beach 2 min walk

4.95 out of 5 average rating, 79 reviews

A private heated pool is surrounded by a spacious patio, offering views of the bay. Lounge chairs are positioned nearby for relaxation. The shimmering water reflects the clear blue sky, creating a serene atmosphere for outdoor enjoyment.

Home in Holmes Beach

Bay beauty with heated pool, spa, games, ping pong

Superhost

Home in Sarasota

5.0 out of 5 average rating, 5 reviews

The Patient Heron | Serene Siesta Key Retreat

4.97 out of 5 average rating, 35 reviews

Manatee Sanctuary - in the heart of Anna Maria

Waterfront condo rentals

4.97 out of 5 average rating, 211 reviews

A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.

Condo in Bradenton

Luxury 3/3 Margaritaville Resort

4.89 out of 5 average rating, 126 reviews

Beachfront Escape – Private Balcony, Gulf Views

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

4.9 out of 5 average rating, 235 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

4.9 out of 5 average rating, 228 reviews

Condo in Bradenton Beach

Gulf Front • Steps to Sand • Sunset Views • AMI

4.85 out of 5 average rating, 121 reviews

A balcony offers a serene view of the Gulf of Mexico, featuring a lounge chair positioned for relaxation. The space is framed by a white railing, with sandy beach and greenery visible in the distance under a bright sky dotted with clouds.

Condo in Bradenton Beach

Oceanfront Condo for Beach Lovers

4.95 out of 5 average rating, 111 reviews

Condo in Madeira Beach

Beach Front at “The Shore”

4.88 out of 5 average rating, 139 reviews

Sunset and beach view from your balcony Unit 403

An aerial view shows a two-story beachfront property with direct access to the beach. A shared pool is visible in the center, surrounded by lounge chairs. The studio unit is indicated with a blue circle on the left, featuring a patio area and proximity to the sandy beach.

4.87 out of 5 average rating, 209 reviews

The Beach Condo #107 Beachfront Full View

Other waterfront vacation rentals

Home in Indian Rocks Beach

5.0 out of 5 average rating, 10 reviews

Harbor Villa | Waterfront Pool & Spa | Firepit

Apartment in Longboat Key

5.0 out of 5 average rating, 36 reviews

New Modern on Beach- Walk out 5 steps to Sand

5.0 out of 5 average rating, 61 reviews

Guesthouse in Anna Maria

The Boathouse

4.88 out of 5 average rating, 58 reviews

Apartment in Anna Maria

Anna Maria 2BR Condo • Walk to Beach, Dining, Pier

A serene canal view is presented, showcasing calm water reflecting vibrant hues of sunset. Lush palm trees and greenery border the serene setting, complemented by a wooden dock extending into the water. The peaceful ambiance invites relaxation and enjoyment of nature.

5.0 out of 5 average rating, 64 reviews

Heavenly Hideaway, 3 bdrm, 5 minute walk to beach

5.0 out of 5 average rating, 15 reviews

Condo in Indian Shores

2BR | Oceanfront, Backyard Beach, Fully Equipped

5.0 out of 5 average rating, 23 reviews

Home in Bradenton Beach

ShoreSideSuites Stunning Gulf Views|Steps to Beach

A spacious outdoor area features a sparkling pool surrounded by lounge chairs and palm trees. A tiki hut provides shade, alongside a putting green. In the background, a rock waterslide is visible, creating an inviting atmosphere for relaxation and recreation.