Holiday rentals with beach access near Anna Maria Island

4.96 out of 5 average rating, 99 reviews

Condo in Holmes Beach

Steps to the beach! Updated Condo at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, coffee maker, blender, balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

Bungalow in Bradenton Beach

A tranquil outdoor space features a wooden dining table surrounded by eight chairs set on a tiled patio. A small, curved swimming pool is framed by lush tropical plants, and umbrellas provide shaded areas. The vibrant greenery creates a serene atmosphere.

4.91 out of 5 average rating, 110 reviews

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

4.99 out of 5 average rating, 163 reviews

Condo in Longboat Key

Beach Condo: Open Tonite, $150/nt + Fees!

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!

The bedroom features a spacious bed with decorative pillows and a light blue throw. An accent bench sits at the foot of the bed, while a round mirror reflects soft lighting from a chandelier. A patterned wallpaper adds a coastal touch, enhancing the serene ambiance.

4.97 out of 5 average rating, 121 reviews

KING Bed + Anna Maria Island Beaches + Beach Gear!

⚓️🦩Welcome to the Coastal Flamingo! Your nautical 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 coastal escape!

4.97 out of 5 average rating, 180 reviews

A heated saltwater pool is surrounded by lush tropical vegetation, creating a serene atmosphere. Poolside seating is offered by several lounge chairs, alongside a shaded area with an umbrella. Sunlight reflects off the water's surface, enhancing the tranquil setting.

Home in Bradenton Beach

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

Townhouse in Holmes Beach

An aerial view captures the coastal neighborhood, showcasing a collection of charming homes with grey rooftops. The vibrant blue ocean and sandy beach are visible in the background, while lush palm trees surround the area, contributing to the serene island atmosphere.

4.99 out of 5 average rating, 149 reviews

Heated Pool & Spacious Lanai! Steps from Beach!

Welcome to Your Dream Beach Escape! Just one block from the sugar-white sands of Holmes Beach, this newly renovated home has everything you need for the perfect getaway. Bikes, paddle boards, and all the beach gear are included for endless fun! Unwind in the shared HEATED pool or soak up the charm of Anna Maria Island. Shopping, dining, and tropical attractions are just a stroll, bike, or trolley ride away. Perfect for families, snowbirds, reunions, and couples!

A three-story coastal home is framed by palm trees, featuring a light-colored exterior. A large balcony is visible on the second floor, and the entrance includes a garage and a fenced area. The setting is serene, highlighting the proximity to the beach.

4.94 out of 5 average rating, 117 reviews

The Peachy Beach House, steps to the gulf

For June, July and August, Saturday to Saturday stays only. If custom trip length is desired, please send inquiry. 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!

Cottage in Bradenton Beach

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.

4.99 out of 5 average rating, 213 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.

Apartment in Holmes Beach

A serene outdoor area features a clear blue swimming pool, flanked by palm trees. Comfortable lounge chairs are positioned alongside the pool, and a shaded dining table is visible in the background. The white exterior of the building reflects a bright, inviting atmosphere.

4.96 out of 5 average rating, 186 reviews

Cabin 2 at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, the free AMI trolley, and nightlife. You’ll love my place because of the location and the ambiance. It is nestled in the lush tropical landscape of Spinnakers Vacation Cottages. You will find Cabin 2 is a perfect spot for an island getaway. My place is good for couples, solo adventurers, families (with kids), and certain size breed and weight dogs. Spa maintains same temperature as pool.

5 out of 5 average rating, 115 reviews

An aerial view captures a serene private pool encompassed by a stone patio, with several lounge chairs arranged nearby. Lush greenery and tropical plants border the scene, while a dark pond reflects the surrounding nature, enhancing a tranquil outdoor space.

Home in Bradenton

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

4.96 out of 5 average rating, 111 reviews

Two bright turquoise adirondack chairs are positioned on a pebbled shoreline, facing a calm canal. Lush palm trees and greenery surround the area, while distant houses line the opposite bank under a clear blue sky.

Home in Bradenton Beach

Waterfront Retreat | Pool • Spa • Dock | Bridge St

🌴 Anna Maria Island Waterfront Oasis! Private dock + heated pool included. Relax by the pool, sip coffee on the dock, or walk just 5 minutes to the Gulf’s sugar-sand beach. Bright, updated home with stocked kitchen, fast Wi-Fi, smart TVs, and cozy beds—perfect for families or couples. Grill by the pool, dine outdoors, or fish from the dock. Boat/kayak friendly. Beach gear + parking included. Your peaceful island escape awaits.

A fire table is positioned in view of a vibrant sunset, reflecting shades of orange, pink, and purple across the sky. The scene is framed by large glass panels, offering unobstructed views of the horizon, enhancing the outdoor experience.

4.91 out of 5 average rating, 136 reviews

New Luxury 3/3 Condo in Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features wonderful unobstructed water views of Anna Maria Sound and Tampa Bay. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

Popular amenities for beach access rentals near Anna Maria Island

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

4.89 out of 5 average rating, 157 reviews

An inviting efficiency unit features a comfortable king-sized bed, two cozy burgundy chairs, and a TV mounted on the wall. A dedicated dining area is visible in the background, alongside a partial view of a relaxing courtyard. Natural light illuminates the room, enhancing its welcoming ambiance.

Apartment in Clearwater

Renovated 2025 - Retro Beach Oasis with Color Pop

4.95 out of 5 average rating, 100 reviews

Apartment in Largo

Hidden Oasis #3, *construction discount!*

Apartment in St. Petersburg

A charming two-story bungalow surrounded by lush greenery and outdoor seating. The entrance features a set of steps leading to a wooden porch, framed by large windows that invite natural light. The yard includes various plants, enhancing the inviting atmosphere.

4.96 out of 5 average rating, 393 reviews

Historic Kenwood Getaway

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, 179 reviews

Beach Front Condo!

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, 114 reviews

Longboat Key-OCEAN FRONT- on the beach

Apartment in Indian Rocks Beach

A view from the balcony captures a stunning sunset over the Gulf, where vibrant hues blend in the sky. The sandy beach is visible below, with a winding path leading to the shoreline. Figures can be seen strolling along the beach, adding life to the serene scene.

4.96 out of 5 average rating, 177 reviews

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

Apartment in Treasure Island

An inviting studio interior is shown with light-coloured walls and a modern kitchenette visible in the background. A doorway leads to a bathroom featuring tropical-themed wallpaper. A small dining table and chair are positioned in front of a cozy seating area with a dark sofa.

4.98 out of 5 average rating, 123 reviews

Popular Beachside Studio w/ Shady Patio & Palms!

Apartment in Indian Rocks Beach

The inviting pool area is surrounded by palm trees and features a vibrant pink flamingo float. Comfortable chaise loungers line the pool deck, offering relaxation options. A wooden fence provides privacy, and the outdoor space is designed for leisure and enjoyment.

4.95 out of 5 average rating, 132 reviews

Triplex across from the beach, heated pool, bikes

Holiday House Rentals with beach access

A charming island home is presented on a landscaped property, featuring a paved driveway with ample space for parking. The elevated structure is accessible by a set of stairs, and palm trees add a tropical touch to the surroundings.

5 out of 5 average rating, 13 reviews

1 block to Pine Ave + Shopping + Beach + Dining!

An outdoor lounge area is showcased under a wooden ceiling, featuring a heated pool and elegant patio furnishings. A television is mounted on the wall, and a dining set is positioned nearby, with a barbecue grill just outside the lounging space, surrounded by tropical landscaping.

5 out of 5 average rating, 51 reviews

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view

The view from the open patio showcases a serene pool area surrounded by palm trees. Two lounge chairs are positioned nearby, inviting relaxation. The space is characterized by a bright and airy feel, with natural light flowing in through large glass doors.

4.91 out of 5 average rating, 23 reviews

Beautiful Pool/Spa, Steps to sand, New Golf Cart

5 out of 5 average rating, 9 reviews

Casa Cay by Duncan Real Estate

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.

4.94 out of 5 average rating, 16 reviews

Bayfront Beach access with Heated Pool!

Superhost

An aerial view captures the property’s prime beachfront location, with expansive ocean views and soft sandy beaches. The serene, turquoise waters of the Gulf are visible, framing the lively beachfront and nearby tropical foliage. Various residential structures are seen dotting the landscape, emphasizing the coastal charm.

5 out of 5 average rating, 4 reviews

Luxury Beachfront Getaway on Anna Maria Island

A cozy outdoor seating area features two blue chairs positioned near a glass-top table with a glowing fire feature. The background showcases serene water views, surrounded by palm trees and residential homes, under a colorful sunset sky.

5 out of 5 average rating, 40 reviews

Elevator, Heated Pool, Dock, Waterfront, Fire Pit

4.98 out of 5 average rating, 46 reviews

Loggerhead - Private Pool + Golf Cart - AMI Oasis

Holiday condos with beach access

A stylish living room is presented, featuring a comfortable gray sofa paired with a decorative round coffee table. Brightly colored wallpaper adorned with shell patterns enhances the space, while large windows allow natural light to filter in, complemented by light-colored flooring.

4.93 out of 5 average rating, 123 reviews

New Renovated Condo + Walk to Bay + 5 Min to AMI

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

4.97 out of 5 average rating, 115 reviews

A&A's Paradise near IMG & Anna Maria beaches

4.88 out of 5 average rating, 119 reviews

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

Sunset and beach view from your balcony Unit 403

4.9 out of 5 average rating, 195 reviews

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

Beachfront Resort, Ocean View, Pool, Tennis, Gym

4.99 out of 5 average rating, 204 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

Spectacular beach to bay views from this resort.

4.95 out of 5 average rating, 146 reviews

Condo in Treasure Island

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

4.91 out of 5 average rating, 196 reviews

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

Beachfront condo in paradise with hot tub

4.99 out of 5 average rating, 144 reviews

A modern kitchen area features pale blue walls and a round dining table set for four. Stainless steel appliances, including a microwave and oven, are visible. A decorative light fixture made of translucent discs hangs above the table, adding a coastal touch to the space.

Condo in Holmes Beach

Short Stroll to the Surf! ~ Make Memories on AMI

Other holiday rentals with beach access

4.99 out of 5 average rating, 87 reviews

The exterior of a modern two-story house is illuminated by soft evening light. A spacious deck is adorned with wooden chairs, and palm trees frame the entrance, enhancing the tropical ambiance. The house showcases a sleek design with large windows and a welcoming entrance.

Home in Bradenton Beach

Gulf Beach Front! Walk to Restaurants + Pier!

A view through large windows showcases lush greenery and palm trees, with glimpses of the ocean in the background. Two comfortable chairs with decorative pillows are positioned invitingly by the window, creating a cozy space to enjoy the scenic surroundings.

5 out of 5 average rating, 37 reviews

Seconds to the Beach! Clean & Cozy NO flood damage

4.99 out of 5 average rating, 77 reviews

A serene backyard pool area is framed by lush palm trees, creating a tropical oasis. A semi-circular seating area under a Tiki umbrella provides a shaded spot next to the pool. Adjacent seating and a grill enhance this inviting outdoor space.

Cottage in Holmes Beach

Brand New Remodeled Villa + Large Private Pool!

A serene outdoor area features a heated pool surrounded by tropical landscaping. Light-colored pavers outline the pool, and large sliding glass doors lead to an inviting sunroom. Towering palm trees provide shade, contributing to the tranquil ambiance.

5 out of 5 average rating, 72 reviews

Private Luxurious Ground Level Home

4.87 out of 5 average rating, 30 reviews

An aerial view captures the vibrant beach community near the coast. The turquoise waters stretch along the shoreline, with sandy beach access visible. Lush greenery surrounds residential structures and shared spaces, including pools, creating a serene coastal environment.

Bungalow in Holmes Beach

Pirate's Den Bungalow steps from Beach Access!

A spacious living area is defined by high ceilings and an open layout, featuring two comfortable sofas facing a wall-mounted television. Large glass doors provide a view of the lush backyard, while decorative plants add a touch of greenery to the room.

4.98 out of 5 average rating, 49 reviews

Unwind Sunshine: steps to locals' favorite beach

Apartment in Bradenton Beach

5 out of 5 average rating, 5 reviews

Beachfront Studio Retreat on Anna Maria Island

A spacious pool area features a large, oval-shaped swimming pool surrounded by multiple lounge chairs. The light-colored patio is lined with tropical plants. A shaded umbrella stands near the seating area, complemented by the inviting blue exterior of the single-level beach house.