Vacation rentals in Holmes Beach

An aerial view showcases a spacious outdoor area featuring a private pool and lounge chairs, surrounded by a gated patio. A light blue house stands in the background with multiple windows, providing a connection between indoor and outdoor spaces. Lush greenery lines the property.

4.94 out of 5 average rating, 34 reviews

Luxury 3BD Beachfront Retreat with Heated Pool!

Sandy Bottoms Beach House is a luxury Gulf-front retreat where modern comfort meets Florida’s natural beauty. With three king bedrooms—each with its own en suite bath—this home is designed for families, couples, or groups seeking a premium beach getaway. Step through oversized sliding doors to a private patio with a heated pool, outdoor dining, and a direct trail to the sand. Spend mornings walking the shoreline, afternoons lounging by the pool, and evenings watching unforgettable Gulf sunsets f

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, 54 reviews

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

Let me know if you need a stay for a period not listed. Unbeatable location, HEATED POOL, ultimate makeover & NEW bedrm, bathrm, lounge, & covered patio additions for spacious beauty are a few things that set us apart! Hidden behind our private gate, the beach is just a few steps away & remains uncrowded-even during busiest season. Premium fixtures, appliances, & plush furnishings create elegance. Garage/parking for 6 cars! Near restaurants, Publix, activities! 30 steps to FREE TROLLEY pick up!

4.96 out of 5 average rating, 101 reviews

Steps to the beach! Condo with pool 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!

A heated pool is surrounded by lush greenery and palm trees. Lounge chairs are positioned along the perimeter, and a gentle blue hue reflects off the water. The two-story buildings in the background create a tranquil resort-like setting.

4.98 out of 5 average rating, 128 reviews

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean and comfortable, my unit at Sandy Pointe II is in a secluded setting just a few minutes walk to a less crowded, quieter section of beautiful AMI beach. From here the Island is at your fingertips! Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! A FREE Island trolly stop is steps from our entrance with grocery, drug store, beach shops and so much more just across E Bay Dr.

An inviting outdoor space features a hot tub illuminated with soft lighting and a waterfall feature. Surrounding the hot tub are four adirondack chairs arranged around a fire pit with flickering flames, creating a cozy atmosphere amidst tropical palm trees.

5 out of 5 average rating, 20 reviews

Black Friday Deals NOW - Holidays at Solace West

This season give the gift that pays great dividends-quality time together. Solace West will provide the perfect backdrop for slowing down, removing distractions and focusing of the ones you love. Whether taking the short walk to the beach and enjoying the many holiday festivities around the island or hopping on the FREE trolley and enjoying the sights and sounds of the holiday, the island will not disappoint. Back at the villa enjoy quiet evenings soaking in the hot tub or sitting by the fire.

5 out of 5 average rating, 42 reviews

Heated Pool, Elevator, Dock, Waterfront, Fire Pit

Escape to The Blue Ark, a unique 3-story home inspired by Noah’s Ark. Families will love this peaceful retreat, blending luxury and comfort. Discover the island's only natural lagoon, boasting stunning views, manatee and occasional dolphin sightings! Unwind by the private pool & spa, fish from the dock, or take an easy 4-5 minute walk to the beach. End the day with a drink by the fire pit on the top deck, watching the sunset. The Blue Ark has an elevator, 3 bedrooms, 8 beds and 4.5 bathrooms.

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.

4.99 out of 5 average rating, 145 reviews

Short Stroll to the Surf! ~ Make Memories on AMI

Nestled in a charming, quiet community of just 8 units, this beautifully updated beach condo offers the perfect blend of relaxation and convenience. The condo is just a short stroll (about 150 steps!) to the pristine white sand beach, where you can soak up the sun and enjoy the coastal views. Wonderful family getaway or couples escape. Private, covered 2 car parking. Laundry in unit. Beach wagon, chairs and gear available. A hidden gem close to everything you need for a relaxing island stay.

Superhost

5 out of 5 average rating, 4 reviews

Heated Pool, Hot Tub, Game Room, Steps to Beach!

Welcome to Island Dreams, the ultimate peaceful escape just 4 min walk from Anna Maria Island's stunning beaches. This fully renovated three-bedroom, three-bath beach house features a Zen-inspired backyard oasis, a private cocktail pool, and a game room! Walk to shops, restaurants, and the trolley stop! Island Dreams offers the perfect blend of relaxation, location, and indoor and outdoor fun! NOTE: Holmes Beach has a 7-day rental minimum. Check in / Check out days are on Saturdays.

A bright living space features light blue walls and natural light streaming through large windows. Two white chairs with starfish cushions are positioned facing a small table. The decor includes small lamps and a decorative sign on the wall, enhancing the coastal ambiance.

4.95 out of 5 average rating, 85 reviews

Island Beach Paradise, Close to Everything, Bikes

This remodeled condo is in the ideal location for your Anna Maria Island getaway. Award winning restaurants, great shopping and a marina are right out your door. The world famous beach on the Gulf of Mexico is three blocks away. Bikes, beach cart, beach supplies are provided. The expansive park across the street has tennis, pickleball, basketball, skate park, playground, dog park, boat & kayak launch ramp. Relax on your deck and enjoy a coffee & the beach breeze through the palm trees.

4.94 out of 5 average rating, 120 reviews

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

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, 152 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!

Superhost

Villa in Holmes Beach

5 out of 5 average rating, 4 reviews

the Seaside 21

The Seaside 21 is a stylish waterfront villa in the heart of Holmes Beach on Anna Maria Island. Enjoy coffee on your private dock overlooking the bayou. Just 4 blocks to the beach, with shops and dining nearby. Bring your boat or have a captain pick you up for a day on the water. This weekly rental has been fully renovated and is centrally located. This island oasis is perfect for relaxing, fishing, exploring, and soaking in everything the island has to offer.

Popular amenities for Holmes Beach vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Holmes Beach's top sights

Anna Maria Island

929 locals recommend

Anna Maria Island Beach

30 locals recommend

Holmes Beach

120 locals recommend

Other great vacation rentals in Holmes Beach

5 out of 5 average rating, 5 reviews

83rd St Villas East by Duncan Real Estate

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

A private heated pool features a waterfall, surrounded by lush tropical landscaping and palm trees. Seating options include teal lounge chairs and white sunbeds, while the pool deck is complemented by a well-maintained lawn area. Colorful plants enhance the tranquil outdoor space.

4.97 out of 5 average rating, 98 reviews

Salty Harbor AMI pool retreat near the Beach

A private heated pool, surrounded by lush tropical landscaping, is complemented by two white chaise loungers positioned beside the water. A propane grill is located on a patio, creating an inviting spot for outdoor dining. The cottage features a vibrant green exterior and large glass doors.

5 out of 5 average rating, 50 reviews

Key Lime Cottage by Beach Boutique Rentals

A private heated pool, approximately 33 feet long, is surrounded by lush greenery. Covered in-pool seating and a small table are visible, along with a patio area featuring an outdoor shower and an umbrella-shaded dining table for six.

4.83 out of 5 average rating, 6 reviews

Turtle Nest! Private Heated Pool and Access to the

4.99 out of 5 average rating, 78 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

Poolside Oasis on Anna Maria Island!

A spacious covered lanai contains a large wooden dining table surrounded by six dark wicker chairs. A ceiling fan provides airflow in the area. Large windows offer views of the private heated pool and tropical landscaping, while the light-colored tile flooring adds a clean, bright appearance.

5 out of 5 average rating, 12 reviews

Private heated pool,2 minute walk to the beach! W