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Beachfront vacation rentals in Anna Maria

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Top-rated beachfront rentals in Anna Maria

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A sandy pathway leads through lush greenery, providing access to a charming two-story building. The structure features a spacious balcony, surrounded by palm trees and local vegetation, under a bright blue sky with scattered clouds.

Apartment in Longboat Key

4.95 out of 5 average rating, 106 reviews

Longboat Key-OCEAN FRONT- on the beach

My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

Top guest favorite

A large window reveals a stunning view of the sunset over the Gulf. Two red adirondack chairs are positioned to face the ocean, inviting relaxation. The soft glow of the setting sun reflects on the water, creating a serene atmosphere in the living space.

Condo in Bradenton Beach

4.91 out of 5 average rating, 185 reviews

Beachfront condo AMI with end of summer discounts

You only have to go down 14 stairs from your second-floor beachfront condo to have your toes in the powder soft sand. A queen size bed with a soft mattress in the bedroom and a queen size pullout couch in the living room. Full kitchen in the unit and laundry available downstairs. Cable and high-speed internet included. One assigned parking spot. Enjoy the sunset from your balcony as it sinks into the Gulf. Perfect for a romantic couple getaway or bring the kids for a fun stay at the beach

A glass sliding door opens to a private balcony, offering views of palm trees and the beach. Outdoor seating is visible, with a chaise lounge beside a small table. The serene ocean can be seen in the background, enhancing the coastal ambiance.

Condo in Longboat Key

4.87 out of 5 average rating, 101 reviews

Beautiful Panoramic Gulf and Sunset Views.

Beachfront Bliss — No Streets to Cross, Just Steps from the Sand! Enjoy breathtaking Gulf and sunset views from your private balcony in this spacious, newly updated condo. Featuring a brand-new bathroom and new flooring throughout, this 4th-floor unit (with elevator access) is the perfect retreat for your Longboat Key escape. The condo comfortably sleeps up to 6 guests. Sip your morning coffee or catch dolphin sightings and stunning sunsets from the balcony with 180° view of the Gulf. Elevator.

A beach scene captured from the water showcases white sand and gentle waves. Several palm trees provide natural shading, while colorful umbrellas appear on the shore. Nearby buildings, characterized by their coastal architecture, complement the relaxed atmosphere of the beach.

Apartment in Bradenton Beach

4.84 out of 5 average rating, 194 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.

A serene beachfront scene showcases soft sand and gentle waves under a clear sky. Lounge chairs are arranged in the foreground, while umbrellas and beach tents are visible further along the shoreline. The bungalow's outdoor seating area is seen, surrounded by lush greenery.

Bungalow in Indian Shores

4.96 out of 5 average rating, 156 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows + heated pool

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.

Condo in Longboat Key

4.92 out of 5 average rating, 179 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.

Top guest favorite

A view from the screened lanai showcases a refreshing pool in the foreground, surrounded by palm fronds and lounge chairs. Beyond the pool, serene blue waters of the Gulf of Mexico are visible, framed by lush greenery and softly swaying palm trees.

Condo in Longboat Key

4.99 out of 5 average rating, 146 reviews

Condo with a View 2: Open Aug 18th-21st, $235/nt!

This charming seaside condo 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 one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

Top guest favorite

A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.

Guesthouse in Bradenton Beach

4.99 out of 5 average rating, 181 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.

A living room area features large sliding glass doors that open to a private balcony with views of the Gulf of Mexico. Soft gray furniture is arranged around a coffee table, and a flat-screen TV is located on a media console. Natural light fills the space.

Condo in Longboat Key

4.87 out of 5 average rating, 107 reviews

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

Top guest favorite

The dining area features a wooden table set for four, complemented by a light fixture above. A comfortable sofa is arranged in the living area, with sliding glass doors providing views of the greenery outside. Artwork adorns the walls, enhancing the ambiance.

Condo in Bradenton

4.98 out of 5 average rating, 214 reviews

Shorewalk full condo IMG Beaches Anna Maria

1174 Sqft first floor 2 bedroom and 2 bathroom with a nice kitchen full condo in the beautiful Shorewalk community. Within very short walking distance to movies, groceries ,shopping and dining This condo is about 9 miles from Sarasota airport and about 13 miles from downtown Sarasota, about 6.8miles from the Bradenton Beach , about 10 miles from Anna Maria Island Less than 1 mile to the big gate of the IMG academy

Top guest favorite

The porch features a circular daybed with decorative cushions, accompanied by a small table and two chairs. Direct views of the bright blue sky and nearby palm trees are visible, enhancing the outdoor relaxation space.

Cottage in Indian Rocks Beach

4.97 out of 5 average rating, 145 reviews

𖤓Updated Stilt home: just steps to the beach!𖤓

Experience a stylish and relaxing beach vacation at our vacation retreat! We are a very popular spot for Honeymooners and anniversaries! As a 4-year Superhost, we offer a charmingly renovated home just steps away from the beach and local restaurants. Explore Indian Rocks Beach with our provided bikes and unwind in the bubbly spa. Escape the everyday and find paradise here! BTR #2292

A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.

Island in Sarasota

4.97 out of 5 average rating, 330 reviews

NEW 3/NTS JULY OPEN! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and 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!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Bungalows

Intimate homes. inviting architecture

Apartments

Convenient locations with everyday essentials

Popular amenities for Anna Maria beachfront rentals

Free parking on premises

Air conditioning

Beachfront home rentals with a pool

An aerial view of the coastline reveals sandy beaches and a vibrant waterfront community. The Marina and several shops and restaurants along Bridge Street are visible, bordered by beautiful green waters. The road runs adjacent to the beach, providing easy access to nearby attractions.

Condo in Bradenton Beach

5 out of 5 average rating, 3 reviews

Cheerful Oasis on Anna Maria Island

A private screened-in pool area features a rectangular pool with an attached hot tub. Surrounding the pool, four lounge chairs in bright colors provide options for relaxation, while tropical plants fill the background, enhancing the enclosed atmosphere.

Home in Longboat Key

4.89 out of 5 average rating, 9 reviews

Beautiful Island Beach House

The image features a clear swimming pool surrounded by sun loungers with umbrellas. Lush palm trees and tropical landscaping are visible in the background, along with a multi-story building. The deck area is paved, and bright blue skies enhance the inviting scene.

Condo in St. Pete Beach

4.85 out of 5 average rating, 124 reviews

1145 Sqft! - 2 Bedroom 2 Bath (GULF FACING!) Condo

A wooden walkway leads from a palm tree-lined entrance to a sandy beach. The ocean is visible in the background, showcasing rolling waves under a clear blue sky. Gentle sunlight illuminates the natural landscape, highlighting the serene environment.

Condo in Bradenton Beach

4.91 out of 5 average rating, 35 reviews

Sandcastle Dreams

A three-story building features multiple glass doors and balconies. A heated pool is situated at the front, surrounded by lounge chairs. The exterior showcases a warm color palette with palm trees visible in the background against a clear blue sky.

Condo in Bradenton Beach

4.89 out of 5 average rating, 47 reviews

Gorgeous Gulf Views - Beachfront 2BR/2B Condo

The image captures a view from the condo balcony, showing a clear blue sky and the tranquil Gulf of Mexico. The pool area is visible, featuring a large swimming pool surrounded by lounge chairs. Beach umbrellas dot the sandy shore, providing a vibrant contrast.

Condo in Indian Shores

4.95 out of 5 average rating, 120 reviews

Tropical Beachfront Penthouse-Beach Cottages #2505

Top guest favorite

The view features a crystal-clear swimming pool framed by tropical landscaping and palm trees. The ocean is visible in the background, beyond the pool area, with beach chairs positioned around the pool for relaxation.

Condo in Holmes Beach

5 out of 5 average rating, 8 reviews

Gulf Place ~ Anna Maria Island, Beach, Pool, Tenni

A spacious heated pool is illuminated with soft lights, creating a tranquil evening ambiance. The surrounding area features lounge chairs, and the ocean is visible in the distance, complementing the serene atmosphere of the outdoor space.

Condo in Treasure Island

4.9 out of 5 average rating, 118 reviews

2/2 Newly remodeled Beach Front - Sunset Vistas

Pet-friendly beachfront home rentals

A serene beach scene shows soft, white sand stretching along the shoreline, meeting gentle turquoise waves under a clear blue sky. A few people are visible enjoying the beach, with vibrant green vegetation and distant structures lining the coast.

Cottage in Pass-a-Grille Beach

4.8 out of 5 average rating, 285 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Cottage in Indian Rocks Beach

4.76 out of 5 average rating, 33 reviews

Yachtsman Gulf front on sand, Sleeps 6 Heated Pool

An airy kitchen area features a large island with a white countertop. Equipped with modern appliances, the space is complemented by a flat-screen TV mounted on the wall. Large sliding doors provide stunning views of the ocean and seamless access to the private balcony.

Condo in Treasure Island

4.84 out of 5 average rating, 120 reviews

Luxury Beachfront Condo Resort Upper Floor

Home in Indian Rocks Beach

4.93 out of 5 average rating, 29 reviews

Indian Rocks Retreat | Panoramic Ocean-View Deck

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

Condo in Clearwater Beach

4.9 out of 5 average rating, 383 reviews

Amazing views on beachfront

The two-story condo building features a light-colored exterior, spacious balconies, and palm trees lining the entrance. The proximity to the sandy beach and vibrant blue Gulf water is visible in the background, showcasing a serene coastal atmosphere.

Townhouse in Indian Rocks Beach

4.96 out of 5 average rating, 121 reviews

♥ OCEANFRONT VIEW ♥ BEACHFRONT CONDO ♥ NEW ♥ U3 ♥

A living room area features a large window overlooking the beach and turquoise waters. Two light-colored chairs are positioned beside a round glass table. A comfortable sofa with decorative pillows is seen, while a lamp provides ambient lighting.

Apartment in Bradenton Beach

4.84 out of 5 average rating, 50 reviews

AMI Bridgeport 203 -Sunset View Retreat+ResortPool

A balcony view captures the sandy beach and turquoise waters, framed by lush greenery below. A few individuals can be seen enjoying the coastline, with palm trees providing shade. The clear blue sky complements the inviting seaside atmosphere.

Apartment in Indian Shores

4.91 out of 5 average rating, 156 reviews

Surfside Villas - Apartment B

Private beachfront home rentals

A beachside area is shown with several white chaise lounges arranged on the sandy surface, facing the ocean. Gentle waves can be seen lapping at the shore under a clear blue sky, accentuated by wispy clouds and coastal grasses in the foreground.

Condo in Bradenton Beach

4.69 out of 5 average rating, 13 reviews

ON THE BEACH Condo, SPA -1 bd/1 ba. Trolley!

Top guest favorite

A soothing pool area features a curved shape, surrounded by a spacious deck and lush greenery. Two lounge chairs sit beside the water, and an umbrella provides shade. Palm trees and tropical plants frame the scene, enhancing the outdoor living space under a bright blue sky.

Home in Sarasota

4.97 out of 5 average rating, 74 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Top guest favorite

A serene ocean view captures the sun setting on the horizon, casting warm orange and gold hues across the sky. Gentle waves break on the shore, creating a foamy shoreline. The tranquil scene highlights the beauty of nature at dusk.

Condo in Redington Shores

5 out of 5 average rating, 12 reviews

Beachfront Condo with Stunning Sunset Views

A screened balcony provides an unobstructed view of the Gulf of Mexico, showcasing vibrant turquoise waters and a sandy beach. Lush greenery borders the foreground, enhancing the serene coastal landscape under a clear blue sky.

Condo in Longboat Key

4.83 out of 5 average rating, 36 reviews

3 BR Condo On Longboat Key Beach and Waterfront

A serene view of a sandy beach meets calm turquoise waters under a clear blue sky. Gentle waves lap at the shore, with soft grasses framing the sandy area, creating a peaceful and inviting atmosphere.

Townhouse in Holmes Beach

4.88 out of 5 average rating, 16 reviews

Miles of Sandy Island Beach

An outdoor patio is featured, surrounded by lush greenery and offering a clear view of the sandy beach and ocean. A round table is set with four chairs, while a lounge chair is tucked nearby. A spiral staircase leads to an upper level, enhancing the space's appeal.

Condo in Belleair Beach

5 out of 5 average rating, 8 reviews

Sonrisa 1 - | Beachfront Condo in Belleair Beach

A dining area features a wooden table set for six with simple dishware. Surrounding the table, woven chairs offer a natural touch. A stone fireplace serves as a focal point, complemented by soft lighting and colorful artwork adorning the walls. An inviting living space is visible in the background.

Home in Indian Rocks Beach

5 out of 5 average rating, 6 reviews

Oceanfront Boho Bungalow Breeze

Top guest favorite

A family beach house is showcased, featuring a main structure with a covered porch and large windows. Adjacent is a smaller cottage. Both buildings have a light-colored exterior and are surrounded by soft sandy ground and palm trees, highlighting the beachfront location.

Cottage in Indian Rocks Beach

4.96 out of 5 average rating, 24 reviews

Kamp Komfort Historic Family Beach House

Quick stats about beachfront rentals in Anna Maria

Total rentals
80 properties
Nightly prices starting at
G$20,920 GYD before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
60 properties have a pool

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