Vacation rentals in Holmes Beach

The living area features light-colored furniture with decorative pillows and wall art. Large windows allow natural light to fill the space, and a cooling ceiling fan is present. A decorative bowl rests on the low coffee table, complementing the warm wood flooring.

4.87 out of 5 average rating, 121 reviews

New Golf cart + 4bd/3b w pool/2100 sq ft home

Urban Oasis is a privately owned 2100 sq ft 4 bd, 3 bth on Anna Maria Island. 4 minute walk on a quiet residential street to walk to the beach.This home features grey blue hues, coastal furniture, driftwood accents, themed rooms and designer accents. A brand new 2024 6 str golf cart is included in your rental as well as a premium linen service including all towels and linens. Urban Oasis is truly a turnkey Vacation Rental! We also have a second property, Urban Oasis Too, if you like our style!

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, 35 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

4.92 out of 5 average rating, 13 reviews

Walk to beach! Private pool! Sea Star Cottage

Private HEATED POOL-two minute walk to the BEACH. 2 bed/2bath home with private backyard and covered lanai. Beautifully decorated and centrally located near shops and restaurants.Enjoy a quiet setting off the main road. Modern amenities and plenty of seating options. Gas grill. Please be a good neighbor by keeping noise levels to a respectable level during the day and night. Excessive noise can deprive neighbors of the peaceful enjoyment of their private property. VRC 19-000082 license #

4.67 out of 5 average rating, 3 reviews

Golf Cart, Dream Weaver by SeaBreeze Vacation

Dream Weaver, offering 3 bedrooms/2.5 bathrooms, is an amazing, custom luxury home nestled in the residential area of Holmes Beach. This home has everything you need for your perfect Anna Maria Island vacation! From the luxurious, resort-style infinity pool that features a separate infinity spa to the putting green. There is also an elevator from the garage to all floors and a full gourmet kitchen. Dream Weaver has an outdoor TV for movies on the patio or watch it from the pool or spa.

4.93 out of 5 average rating, 122 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

4.98 out of 5 average rating, 60 reviews

A spacious living area features a modern sectional sofa with plush cushions in neutral tones. A circular coffee table rests on a soft area rug. A vibrant grass wall adds a touch of greenery, while a dining table with chairs is visible in the background.

Condo in Holmes Beach

Luxury 2BR Oceanfront Condo + Rooftop Patio

Modern Condo with Stunning Ocean Views: - Cozy turf patio - Smart TVs and high-speed WiFi - Fully equipped kitchen - Two private parking spots for hassle-free stays - Just a 2-minute walk to the beach Unique Features: - Social Media worthy grass wall - Two comfortable beds: one king & one queen, ensuring a restful sleep - Queen-sized inflatable extra bed Prime Location: - Conveniently located next to the AMI trolley stop - Within walking distance to dining, a gym, and more!

4.88 out of 5 average rating, 178 reviews

A charming cottage is set against a vibrant blue exterior, featuring a thatched umbrella over a small outdoor seating area with four chairs. Lush green shrubs and sandy pathways enhance the inviting entrance, while palm trees are visible in the background under clear blue skies.

Bungalow in Anna Maria

Bay Breeze Cottages #2

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

A light-filled living area features a comfortable, neutral-toned sofa adorned with textured pillows. A wooden coffee table rests on warm-toned flooring. The space includes a cozy lamp and a small dining area with two stools, complemented by natural decor elements on the walls.

5 out of 5 average rating, 13 reviews

Charming houseB 2 min walk to beach, 4+, baby pets

Modern & comfortable 2-bedroom, 2-bathroom stay is a short couple minute walk to the white sand beach of Anna Maria Island. The fully equipped kitchen has modern appliances, and the open layout provides plenty of space to relax. Step outside onto private outdoor space to enjoy a morning coffee, sit and relax, or grill! Newly outfitted for the 2025 season, with brand-new furnishings, linens, and everything you need for a comfortable stay. Side-by-Side Units – Book One or Both!

Apartment in Holmes Beach

4.78 out of 5 average rating, 306 reviews

Ohana Hale North B - 1 Bedroom

Aloha and welcome to our Island Home - Your Ohana Hale Ohana is Hawaiian for family and that is who you are when you stay with us. This one bedroom suite is idea for a couples getaway or small family vacation. Our retreat is nestled on Anna Maria Island, Florida and is a short 7 minute walk to the white sand beaches and turquoise waters. This apartment has a 7 night minimum stay requirement but we have other great properties if you need a shorter stay, just contact us!

5 out of 5 average rating, 7 reviews

Home in Anna Maria

Mermaid's Treasure by Duncan Real Estate

Welcome to Mermaid's Treasure! A fabulous North-end beach vacation home with a private swimming pool, hot tub, and plenty of space for entertaining friends and family. This 2 bedroom and 2 bath getaway is just a quick walk away from pristine Gulf of Mexico beaches and is close to the famous Pine Ave, offering unique restaurants and shopping experiences. As you walk in, you'll notice the lovely beach vibe with a casual living area with comfy seating and a TV.

A tranquil outdoor area features a swimming pool surrounded by lush palm trees and tropical plants. Two loungers invite relaxation beside the water, and a dining table is set for outdoor meals. Sunshine brightens the scene, enhancing the inviting ambiance.

4.98 out of 5 average rating, 161 reviews

Captain's Quarters at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love my place because of the high ceilings, the location, and the ambiance. It is located in the lush tropical paradise of Spinnakers Vacation Cottages. With a large living room, dining area and large master suite, it is perfect for couples, families (with kids), and furry friends (dogs, with a small pet fee). Captains Quarters also has Private patio!

4.75 out of 5 average rating, 4 reviews

AMI Sunset~Close to beach! Heated Pool!

A charming three-bed, two-bath beach house on Anna Maria Island, this coastal retreat offers a heated pool, two king rooms, and a fun bunk room. Just steps from the beach, it delivers unforgettable sunrises and sunsets. Beautifully designed for comfort and relaxation, it’s the perfect island getaway for families or friends looking to enjoy the best of AMI.

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

967 locals recommend

Anna Maria Island Beach

31 locals recommend

Holmes Beach

121 locals recommend

Other great vacation rentals in Holmes Beach

Apartment in Bradenton Beach

A bright living area features turquoise walls and natural light streaming in through multiple windows. A comfortable gray sofa and a vibrant yellow accent chair provide seating. A wooden dining table with white chairs offers a space for meals, while a coffee table sits in the center.

5 out of 5 average rating, 16 reviews

Coconut Vacation Rentals/1BR/Pool/Steps to Beach!

Townhouse in Holmes Beach

A sandy beach extends towards a calm ocean, where turquoise waters meet a clear blue sky. Colorful umbrellas provide shade for beachgoers, who are relaxing on vibrant towels. The shoreline features soft white sand, inviting visitors to enjoy the peaceful environment.

4.93 out of 5 average rating, 57 reviews

Getaway Family Beach Townhome w/Pool!

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, 53 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.

4.89 out of 5 average rating, 9 reviews

Turtle Nest! Private Heated Pool and Access to the

4.95 out of 5 average rating, 41 reviews

A cozy bedroom features a spacious bed with light bedding, accented by decorative pillows. Natural light streams through sheer curtains by the window, illuminating the room's soft blue walls. A wooden dresser and a ceiling fan add functional elements to the friendly space.

Villa in Holmes Beach

Starfish House - 2bed/2bad

Apartment in Bradenton Beach

5 out of 5 average rating, 6 reviews

Semi Private Pool -Beach Gear Provided - 3Bedrooms

The exterior of a newly remodeled villa is displayed, featuring a front balcony with white railings and lounge chairs. Lush tropical plants surround the home, and clear blue skies complement the light-colored façade. The space below offers covered parking, enhancing convenience.

5 out of 5 average rating, 25 reviews

Sandy Toes

A spacious living area features two yellow sofas accented with vibrant patterned cushions. A wooden coffee table sits atop a patterned area rug with palm leaves. A colorful abstract wall art piece is displayed above the seating, and a standing lamp adds an inviting touch.