House holiday rentals in Holmes Beach

4.97 out of 5 average rating, 118 reviews

A charming cottage is set among greenery, featuring a covered carport and a gravel driveway. An American flag is displayed on the front porch, alongside a large circular window. Lush trees and shrubs surround the home, creating a welcoming outdoor area.

Home in Palmetto

The Island-Hopper's Haven Near Anna Maria Island

Discover vintage charm & modern luxury in this cozy Palmetto cottage. Perfectly located at the heart of Florida's Gulf Coast, you can access St. Pete, Anna Maria Island, Sarasota & Fort DeSoto within 30 mins. You can explore nearby Emerson Pointe Preserve's hiking & kayak trails. You'll be minutes away from Downtown Palmetto & Bradenton's many dining & nightlife options. Boating enthusiasts will love the proximity of the Palmetto public boat ramp. Reserve now & experience Florida's Gulf Coast!

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, 198 reviews

Be an 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 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, 116 reviews

Breezy Harbor AMI pool retreat near the Beach

Charming Breezy Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -We typically have shorter stays available, just ask! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

5 out of 5 average rating, 43 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.

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, 22 reviews

Sandy Toes

This newly remodeled, upscale villa is on a quiet island street less than 300 steps from the powder white beach of Anna Maria Island. Over a dozen restaurants within a quarter of a mile short stroll and many shops close by to visit as well. The private villa includes a "treetop" front balcony which is a guest favorite to enjoy gulf breezes & relaxation. A fabulous, covered side porch overlooks extensive tropical plants and set up with comfortable chairs and your own private gas weber grill.

A winding stone path is bordered by lush greenery, leading through the expansive yard surrounded by tall trees. Various native plants are visible, creating a natural and serene environment.

4.8 out of 5 average rating, 233 reviews

Charming Beach house amongst huge Banyon Trees

Charming bright beach house set amongst grand Banyan trees on tip of Anna Maria. 3 min's stroll over a small fishing bridge to historic Pine Ave w/ quaint eateries and shops. Huge fenced yard voted "A Tropical Paradise" Porch sits among huge banyan trees with native birds. 7 min’s walk to bay front beach or rod and reel pier for fresh meals, cocktails, fishing w/ equip & bait supplied, from there stroll along The beach to "Bean Point" voted 1 of the most beautiful beaches in the world.

5 out of 5 average rating, 9 reviews

New! Heated pool/Spa~Water Slide and Grotto! Views

Welcome to Harbor Haven, a stunning vacation rental nestled in the heart of Anna Maria Island. This 4-bedroom, 7-bathroom oasis is just a 5-minute stroll from the pristine Gulf beaches. Immerse yourself in the ultimate relaxation with our gorgeous freeform pool, complete with a hot tub, waterfall, water slide, and grotto for endless fun and tranquility. Whether you're lounging in the sun or enjoying a family barbecue, Harbor Haven offers the perfect backdrop for unforgettable memories.

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

An inviting exterior view of Sunrise Villa showcases a well-maintained landscape featuring lush greenery and vibrant plants. A spacious driveway leads up to a garage, with decorative stone detailing accentuating the garden area. The home is framed by palm trees, contributing to the tropical ambiance.

5 out of 5 average rating, 109 reviews

Sunrise Villa - Tropical 3 bedroom home with pool

Relax with the family at this tropical oasis. Sunrise Villa sits in the corner of a quiet cul-de-sac, just a quarter mile from Palma Sola Bay and 5 miles from the quaint island of Anna Maria and its sandy white beaches. Enjoy the tropical backyard paradise and the abundance of restaurants, beaches, and entertainment in close proximity. Lounge by the pool, take a bike ride along the bay, take a short bike/car ride over to the island, or take a short car ride to downtown Bradenton.

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, 146 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.

A comfortable living area features a dining table for four and a cozy seating arrangement. Light streams in through sliding glass doors, leading to the balcony. A houseplant adds a touch of greenery, while a mounted TV is positioned against a shiplap wall.

4.94 out of 5 average rating, 33 reviews

* Anna Maria Sunrise Escape A *

Discover the perfect beachside escape at our centrally located 2-bedroom haven on Anna Maria Island, just steps from the sand and some of the island's top amenities! 1 Block to the Beach! 2 Bed / 1 Bath 2 Kings Balcony with Patio Furniture Dining Table for 4 & 2 Counter Bar Stools Washer & Dryer on-site WIFI Elevated Beach House (Duplex) Beach Towels & Chairs Gas Grill - (shared) Parking for 2 Cars, Including 1 enclosed garage space

4.99 out of 5 average rating, 120 reviews

A bright kitchen is showcased, featuring modern cabinetry and appliances. A small dining area with two wooden stools is positioned next to a white countertop. Natural light fills the space through a nearby door and window, creating an open atmosphere.

Home in Cove

Tranquility on the bay.

Tucked away from the hustle and bustle, my mobile home is located in a very unique neighborhood right on the bay with a little beach 2 min. down the road from my house, where you can sit and enjoy the views or fish. The homes are a combination of mobile homes like mine and houses with the most wonderful people of all walks of life. Very quiet, very safe and friendly. 5 min. to Bradenton beach and 10 min. to AMI.

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, 16 reviews

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

5 out of 5 average rating, 4 reviews

Island Vibe 3

A private pool area is surrounded by tropical landscaping and features clear blue water. The pool is equipped with a ladder and a spacious deck with outdoor seating. A light-colored duplex with large windows is visible in the background, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 144 reviews

Blue Bungalow B

4.93 out of 5 average rating, 176 reviews

Casa Noir | POOL • BBQ • FIRE PIT • GAMES • VIBES

A private heated pool is surrounded by lush tropical landscaping and features a stone border. A patio area with outdoor furniture is positioned nearby, while palm trees gently sway in the breeze. The bright blue sky enhances the serene atmosphere of the space.

4.83 out of 5 average rating, 24 reviews

Cozy Cottage - POOL HOME! 3/3

4.78 out of 5 average rating, 18 reviews

2 min walk to Holmes Beach - Walk to Shops, Dining

A serene backyard features a heated pool surrounded by lounge chairs and shaded areas. Tropical plants and flowers add color, while the setting sun casts a warm glow. Umbrellas provide shade over the seating, creating a welcoming space for relaxation and outdoor enjoyment.

4.97 out of 5 average rating, 107 reviews

Orange Oasis: Clean, heated pool, near beaches.

A charming outdoor area showcases a refreshing pool accompanied by a built-in hot tub. Comfortable lounge chairs are placed around the pool, complemented by a large red umbrella providing shade. Lush palm trees and a white fence enhance the tropical ambiance of the space.

5 out of 5 average rating, 7 reviews

Fanta Sea | Island Fun w/Pool, Hot Tub, Game Room!

Weekly house rentals

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, 39 reviews

Seconds to the Beach! Clean & Cozy NO flood damage

A spacious outdoor area features a heated saltwater pool and a spillover spa, surrounded by a large screened lanai. Multiple seating and dining options are available, with tropical decor enhancing the space. Expansive glass doors provide seamless access to the indoor living areas.

5 out of 5 average rating, 90 reviews

NEW saltwater pool/spa! Free pool heat!

A spacious kitchen is highlighted by modern appliances and a large island with seating for four. White cabinetry and light countertops create a bright atmosphere, while two pendant lights hang above the island. Large windows allow natural light to fill the room.

5 out of 5 average rating, 5 reviews

Luxury Home•Steps to Gulf•Sunsets & Beach Walks!

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.

4.96 out of 5 average rating, 23 reviews

Ocean Air Oasis-New Centrally Located AMI Luxury

5 out of 5 average rating, 4 reviews

Newly Listed +Close to Beaches+Sits on Canal View

The image depicts a bright, two-story beach house with light blue siding, surrounded by palm trees and lush greenery. A white picket fence lines the front, offering a sense of privacy. The sky is clear with soft clouds, conveying a tranquil coastal atmosphere.

5 out of 5 average rating, 64 reviews

Luxury Home Steps to Quiet Beach on 78th St

A dining area features a large wooden table surrounded by white chairs and a long wooden bench. A vibrant area rug adds color, while a mural of palm trees against a sunset creates a relaxed atmosphere. Natural light filters through the window, illuminating the space.

5 out of 5 average rating, 25 reviews

Anna Maria Aloha – Pet Friendly, Steps to Gulf

5 out of 5 average rating, 6 reviews

Beautiful Beach house! Heated pool and spa!

Private house rentals

A private pool area features a clear blue pool bordered by neutral stone tiles. Two lounge chairs with towels are positioned beside the pool, surrounded by lush greenery and palm trees. A covered deck is visible above, offering a shaded retreat.

4.98 out of 5 average rating, 43 reviews

AMI Sand Dollar

A private saltwater pool is framed by swaying palm trees and a sun shelf. Two lounge chairs are positioned nearby for relaxation. The surrounding space is brightened by natural sunlight, with a white fence and lush greenery enhancing the serene atmosphere.

5 out of 5 average rating, 52 reviews

Modern 3BR Retreat + Anna Maria Beaches + IMG!

4.83 out of 5 average rating, 148 reviews

Two wooden beach chairs are placed under a large blue striped umbrella, with a cooler positioned between them. The serene turquoise waters and sandy beach create a relaxing coastal scene, with gentle waves lapping at the shore.

Home in Bradenton Beach

50 Steps to Beach Villa Hot Tub 1bd modern cottage

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.

4.95 out of 5 average rating, 19 reviews

Bayfront Beach access with Heated Pool!

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!

5 out of 5 average rating, 3 reviews

Cozy Beach Cottage, Pet Friendly

The duplex features a light blue exterior with a welcoming porch adorned with yellow and blue chairs. Lush palm trees and vibrant landscaping enhance the outdoor space, while a clear blue sky adds brightness to the scene. Graveled parking is visible in front of the unit.

4.94 out of 5 average rating, 98 reviews

Do you love the beach?

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.