House holiday rentals in Holmes Beach

A private heated pool is surrounded by tropical landscaping and palm trees, creating a serene outdoor space. Two lounge chairs are positioned beside the pool, and a small table is visible on the lawn. Bright sunlight casts a warm glow over the vibrant plants.

4.95 out of 5 average rating, 111 reviews

Breezy Harbor AMI pool retreat near the Beach

Stunning Fall 2024 renovation done! Charming Breezy Harbor boasts a private heated pool and sits on a quaint corner of AMI. Upon arriving you will immediately feel stress melting away. You'll love grilling in the lush yard and a 6-min walk to the beach or the AMI trolley stop. A supermarket is a couple of streets over. The home is perfect for families, couples, 1-50Lb pet, and working remotely. Ample Parking for 2 vehicles and toys. *Ask us for shorter stays and always discuss your pets with us*

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, 31 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, 49 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!

A charming beach house is nestled among tropical palm trees, featuring a light grey exterior with white accents. The elevated design includes two garage doors and a spacious balcony, inviting natural light into the upper level windows. A sandy path leads to the entrance.

5 out of 5 average rating, 11 reviews

Pineapple Paradise~WATER SLIDE/ Heated Pool & Spa!

Enjoy the waterslide heated pool home! Perfect for adults & kids of all ages. Owner managed. This exceptional 4 bed, 6 & 1/2 bath vacation home is just a few steps away from the beach. To provide guests with an unforgettable experience, we have designed this house with a perfect backyard for entertaining & an incredible rooftop deck that offers stunning views of the Gulf! • Owner Managed • Rooftop deck • Private pool with waterslide & spa • Outdoor living space • Foosball/Ping Pong • Connect 4

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

Seconds to the beach! NO flood damage. Photos current & accurate. Watch the sunset from the house! 3-bed, 2-bath, multi-level fun-house on a large shady lot in a quiet residential neighborhood. 2 blocks from popular shopping & dining, so there’s always something fun close by! Fully equipped kitchen with all you’ll need for island cooking & entertaining. Comfortable dining for 8. Beach chairs, umbrellas, cooler & beach cart with large inflated wheels for rolling easily over beach sand.

A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.

4.96 out of 5 average rating, 196 reviews

Sea AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

A private lagoon-style pool is surrounded by lush tropical landscaping. A small rock waterfall flows into the gently curved pool, which is complemented by comfortable seating. Sunlight filters through the foliage, creating a serene outdoor retreat.

4.97 out of 5 average rating, 143 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly just 5 min. walk to the beach. Private lagoon-style *heated* saltwater/low chlorine pool amid lush landscaping with gorgeous rock waterfall. New appliances, HVAC, 60-inch Sony HDTV, Italian leather reclining sofas, BBQ, beach gear, three king bedrooms, all linens provided. Classic Florida one-level home - no stairs. Managed directly by owners, so no crazy fees.

4.97 out of 5 average rating, 179 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.

4.96 out of 5 average rating, 110 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 Gem/ Pool Spa+ Dock/ Near Bridge Street

Anna Maria Waterfront oasis! **5 min walk to beach, private dock, pool heat included!!** Relax in the private heated pool, sip coffee on the dock, or walk to the beach. This bright, updated home has spacious living areas, a stocked kitchen, smart TVs, fast Wi-Fi, and cozy beds. Great for families or couples! Grill by the pool, dine under the stars, or fish from the dock. Includes washer/dryer, beach gear, and parking. Your peaceful, sunny getaway awaits—book now!

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, 160 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!

The open-concept living area features a modern dining table set with intricate lace placemats. A pink sofa and white chairs provide ample seating, complemented by a stylish chandelier overhead. Bright natural light fills the space, highlighting decorative plants and framed artwork.

5 out of 5 average rating, 84 reviews

Wanderlust Villa

Welcome to Wanderlust Villa! This Anna Maria beachside beauty is a chic slice of paradise on AMI. Hues of pink and gold give the villa a warm and cozy yet ultra-chic vibe. It’s a total INSTA-WORTHY space! Wanderlust Villa is a quick half-mile walk to the beach and a 10 minute walk to a variety of restaurant options. Your gulf-view sunsets are waiting for you! 🩷 Any questions or booking requests outside of what is outlined please message!

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.

5 out of 5 average rating, 18 reviews

L'Oasis East w/Dip Pool

Completely remodeled, this beautifully 2-bedroom duplex, crafted to enhance your living experience. Every detail has been thoughtfully designed to create a serene and inviting atmosphere. New images showcase this stunning transformation, come visit us to see the beauty in person! Additionally, West and East are now available for rent together, featuring convenient adjoining doors through the utility room.

Popular amenities for house rentals in Holmes Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 12 reviews

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

The image shows a two-story home surrounded by lush greenery and mature palm trees. A stone pathway leads to the entrance, highlighting the well-maintained lawn and landscaped garden. A balcony is visible on the upper level, enhancing the inviting exterior.

4.87 out of 5 average rating, 30 reviews

Sweet Sea Life - just a short walk to the beach

An outdoor view showcases a private pool surrounded by lush landscaping and tropical palm trees. The distant beach features soft white sand meeting turquoise waters. A spacious deck, complete with loungers, offers a perfect relaxation spot under clear blue skies.

4.91 out of 5 average rating, 65 reviews

TOES IN THE SAND!

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.

4.93 out of 5 average rating, 15 reviews

Bayfront Beach access with Heated Pool!

An open living space features a light-colored couch and a matching loveseat, complemented by decorative pillows. Natural light fills the room through large windows adorned with sheer and blackout curtains. A marble countertop provides a dining area with elegant place settings, inviting relaxation and conversation.

4.87 out of 5 average rating, 15 reviews

Tranquility Meets Style-Walk to beach-prvt pool.

An aerial view of a charming ground-level vacation home is presented, featuring a light-blue exterior and a metallic roof. Surrounded by lush tropical landscaping, a clear pool reflects the sunlight, and a patio area with lounge chairs is visible in the background.

5 out of 5 average rating, 16 reviews

Sea Shack - 2bd/2ba POOL Home

4.98 out of 5 average rating, 80 reviews

Calico AMI – Steps to Sand, Family Paradise!

A charming beach house is surrounded by lush palm trees and tropical landscaping. The exterior features a light blue color, and balconies are visible on the upper level. A paved pathway leads to the front entrance, creating an inviting approach.

4.94 out of 5 average rating, 50 reviews

Anna Maria - 3 Bd 2 Bth-Heated Pool-Walk to Beach

Weekly house rentals

4.81 out of 5 average rating, 54 reviews

Large House, Heated Pool, 5 houses to Beach!

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, 11 reviews

NEW Charming Coastal, so close to beach!

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.

5 out of 5 average rating, 12 reviews

The Shell House

A private backyard features a curved pool surrounded by tropical landscaping. A thatched tiki hut provides shade over a dining table, while a large umbrella shades additional seating. A flamingo float is visible in the water, enhancing the relaxed outdoor atmosphere.

4.78 out of 5 average rating, 18 reviews

Steps Away from the Sandy Shores of Holmes Beach!

A spacious living area is filled with natural light from large windows. A comfortable sectional sofa is arranged with decorative pillows, complemented by a wood coffee table at the center. Two soft reclining chairs are positioned nearby, contributing to the inviting atmosphere.

5 out of 5 average rating, 16 reviews

Summer Discount Rates- steps to the beach.

5 out of 5 average rating, 58 reviews

A large heated saltwater pool is enhanced by colorful floating rings. A waterfall feature adds a calming effect while lounge chairs are positioned nearby. The patio area is visible, furnished with multiple seating options, and surrounded by lush greenery and sunny skies.

Home in Bradenton

NO FEES | Heated Pool | Game Room | Sleeps14 | BBQ

5 out of 5 average rating, 3 reviews

NEW - The Salty Palm - nearby beach, shops, food!

A soothing hot tub is featured alongside a gently curving pool surrounded by lush tropical landscaping. The space is enhanced by palm trees and vibrant plants, visible beside the pool deck. Sun loungers are placed nearby, inviting relaxation in the serene outdoor environment.

5 out of 5 average rating, 5 reviews

Ground Floor Luxury 1Bdr. Home, Heated Pool/Spa

Private house rentals

A private backyard features a heated pool surrounded by tropical palm trees. Comfortable seating areas are located on the deck, complemented by a grill nearby. The pool area is highlighted by a spacious lounge area with sun chairs and a shaded umbrella.

5 out of 5 average rating, 3 reviews

Colorful Beach Cottage with Heated Pool and Walk

An aerial view captures the coastline, highlighting the proximity to the water, located approximately 100 yards away. The image showcases the vibrant blue of the ocean alongside the sandy shoreline, with the surrounding community visible in the distance.

5 out of 5 average rating, 8 reviews

Relax at Bryant's Beach Bungalow!

An inviting hot tub with vibrant blue lighting is framed by wooden beams, creating a sheltered space for relaxation. The heated saltwater pool is visible in the background, surrounded by lush greenery and a white fence, enhancing the tranquil atmosphere.

4.89 out of 5 average rating, 55 reviews

Backyard Bliss Anna Maria Island

5 out of 5 average rating, 5 reviews

While Away A: Beach Bliss Reimagined

The exterior of the duplex displays a light green façade, framed by palm trees and tropical plants. Two white adirondack chairs are arranged on a stone pathway, leading to the entrance. A decorative element with fish artwork is mounted on the wall near the entrance.

4.9 out of 5 average rating, 20 reviews

Blue Bungalow A

An aerial view showcases a coastal neighborhood with palm trees and sandy paths leading to the beach. The two-story home features a gray exterior and a deck visible on the side. The turquoise waters of the Gulf are seen in the background, enhancing the beach atmosphere.

5 out of 5 average rating, 8 reviews

1 Block to Beach ~ 3BR Coastal Retreat with Pool

An aerial view of a tranquil beach stretches along the coastline, featuring gentle waves lapping at the sandy shore. Umbrellas and beach chairs are scattered across the sand, while residential buildings and greenery are visible in the background, providing a peaceful seaside setting.

4.75 out of 5 average rating, 12 reviews

Reese's Beach Retreat