Beachfront rentals near Anna Maria Island

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals near Anna Maria Island

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Four colorful Adirondack chairs are arranged on a grassy area, facing the ocean. A small table is positioned between the chairs, with the blue skies and calm waters visible in the background.

Home in Anna Maria

5 out of 5 average rating, 6 reviews

Casa Cay by Duncan Real Estate

Welcome to Casa Cay! This Bay front pool home on Anna Maria Island sounds like an absolute paradise! With its prime location on the North end between the 2 piers, stunning views of the bay and the Sunshine Skyway, and direct access to a private bay beach, it offers the quintessential island experience. The layout of the house, featuring three bedrooms and three bathrooms, including two suites with ensuite bathrooms, sounds perfect for families or groups of friends looking for comfort and ...

Top guest favorite

A pool area is featured, showcasing a circular hot tub adjacent to a larger pool surrounded by tropical foliage. The two-story house is visible in the background, with an American flag displayed on the balcony. Outdoor lounge chairs are arranged near the water.

Home in Anna Maria

5 out of 5 average rating, 14 reviews

CabAnna Maria Beach Block 4 Bedroom 4.5 Bath

CabAnna Maria is a newly renovated 4 bedroom, 4.5 bath house, that sleeps 8 (max) comfortably, a quick 450 ft to the pristine sands of AMI beach. 3 king bedrooms w/ en-suite baths and large TVs. 4th bedroom has a twin over full bunk. Common bath has a tub. Open spacious living room w/large comfy couch and a 75" TV. 1/2 bath on pool level, cabana with TV, sink & fridge. Beach chairs, umbrellas, bikes, SUP, kayak & more. Linens, beach towels and toiletries provided. Managed by Doreste Properties

Guest favorite

A sandy pathway is framed by tall grasses leading to a beach with gentle waves. Sun loungers are visible along the shore, while the bright blue sky features a few scattered clouds. The peaceful scene highlights the natural beauty of the coastline.

Apartment in Holmes Beach

4.95 out of 5 average rating, 38 reviews

AMI Ohana Beach Resort A with fabulous salt pool!

The location is perfectly situated in the middle of the island with quick access to the beach (3 minute walk from door to shore without crossing Gulf Drive), Publix grocery store, Walgreens, Manatee Public Beach, shopping, restaurants and more. The free trolley stop is steps away offering an affordable way to explore the whole island. Ohana Beach Retreat is a newly renovated triplex in Holmes Beach on Anna Maria Island. Come enjoy our heated salt water pool in an oasis of palm trees.

Guest favorite

The outdoor area features a spacious pool and a separate spa, surrounded by manicured gardens and palm trees. A covered lanai with steps leads to the upper level of the home, which includes expansive sliding glass doors inviting natural light into the interior.

Home in Anna Maria

4.94 out of 5 average rating, 18 reviews

Ocean Air Oasis-New Centrally Located AMI Luxury

Immerse yourself in coastal luxury at this exceptional 3-bedroom, 2.5-bathroom custom home, where opulent high-end finishes and stunning pecky cypress floors adorn every nook. Revel in the impeccable features, including Sub-Zero and Wolf appliances, marble countertops, Shaw’s sinks, and exquisite custom woodworking, all bathed in abundant natural light. This delightful space offers panoramic views of the lavish backyard, complete with a heated pool and spa.

Top guest favorite

A vibrant yellow cottage is surrounded by a sandy area with palm trees. Colorful adirondack chairs in pink, blue, and green are positioned on the white gravel. A covered outdoor seating area is visible to the side, enhancing the beachside environment.

Cottage in Bradenton Beach

4.98 out of 5 average rating, 179 reviews

Bradenton Beach Sunsets 2, 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.

Guest favorite

An oceanfront balcony offers expansive views of the sandy beach and calm waters. Beach chairs are positioned on the shore, complementing the serene atmosphere. Clear blue skies reflect on the water, enhancing the peaceful setting of this beachfront escape.

Condo in Madeira Beach

5 out of 5 average rating, 30 reviews

Oceanfront Loft w/ 2 Baths in Madeira Beach

Experience beachfront luxury at this stylish 1-bedroom loft in Madeira Beach. Perfect for couples or small families, it features a king bed in the loft, two full bathrooms, and a Murphy bed in the living area. Enjoy ocean views from the private balcony, a full kitchen, and convenient washer and dryer. Spend your days on the sand or exploring nearby attractions like John's Pass Village. A serene coastal retreat for a memorable getaway.

Guest favorite

The front view of a three-story home features a light-colored exterior with decorative detailing. Large windows allow for ample natural light. Lush palm trees frame the entrance, and a garage is visible below, indicating convenient parking options.

Home in Holmes Beach

4.94 out of 5 average rating, 107 reviews

The Peachy Beach House, steps to the gulf

Hurricane season cancellation possible. Saturday-Saturday for check-in and out. Two bedroom, 2 full bathroom, new heated private pool Steps from semi-private gulf beach, this 3 story on a quiet street in N. HB Well-stocked kitchen, 2 TVs, large master which is more like resort suite with new tempurpedic king bed Gulf views from bedrooms. You’ll find: crib, high chair, beach chairs, wagon, canopy, beach toys and towels!

Guest favorite

A thatched-roof pavilion with a picnic table is set by the poolside, offering a shaded spot for gatherings. The shimmering pool reflects clear blue skies, and the beach is visible in the background, framed by lush greenery and swaying grasses.

Apartment in Belleair Beach

5 out of 5 average rating, 14 reviews

NEW Beachfront Oasis with Pool in Belleair Beach

BEACH ACCESS a few steps away from your front door! Views of the beach included with an in-ground pool and picnic area on one of the most beautiful beaches on Florida's Gulf Coast! Our fully renovated apartment is fully equipped with a combo kitchenette, dining space, living room with smart tv, and bedroom with smart tv. If you're looking for a peaceful and fun beach getaway, you've come to the right place!

Top guest favorite

A cozy master bedroom features a spacious bed adorned with soft linens and decorative pillows. Two bedside tables with lamps flank the bed, and artwork of serene coastal views is displayed above. Light is provided by inset ceiling fixtures, enhancing the calming atmosphere.

Guesthouse in Anna Maria

5 out of 5 average rating, 31 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.

Guest favorite

An outdoor area features a crystal-clear pool surrounded by paver stones. A set of six wooden chairs and a table are positioned nearby, complemented by two lounge chairs. The exterior of the vacation home displays a vibrant blue-green facade with large windows reflecting the sunlight.

Home in Anna Maria

5 out of 5 average rating, 8 reviews

Sea Shack - 2bd/2ba POOL Home

Welcome to Sea Shack, an inviting ground level vacation home with a pool just steps away from the beach! Visit Pine Ave’s locally-owned boutiques and restaurants just a five-minute walk away. This rental accommodates up to 6 guest. Fully equipped kitchen has plenty of storage space for all your cooking necessities. Baby accessories available for rent: Snoo bassinet High chair Pack and play

Guest favorite

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, 327 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!

Superhost

A private heated pool is surrounded by tropical palms, featuring a gently curved shape with clear blue water. Two white adirondack chairs are positioned nearby on a paved patio, inviting relaxation in a tranquil outdoor setting.

Home in Anna Maria

5 out of 5 average rating, 6 reviews

The Shell House

Adorable 2 bedroom, 2 bath beach cottage with private, heated pool. Located on the north end of the island and only 3 houses from the beautiful white sand beach of Anna Maria Island. Relax and unwind in the spacious pool, surrounded by tropical palms. The cottage has a large covered and screened patio in the backyard by the pool.