House holiday rentals in Holmes Beach

5.0 out of 5 average rating, 65 reviews

Waterfront, Heated Pool, Elevator, Fire Pit, Dock

Escape to The Blue Ark, a 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 heated pool, 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 + extra sleep space, 8 beds and 4.5 baths.

5.0 out of 5 average rating, 13 reviews

Carissa A | Beachside Retreat | Golf Cart | Pool

Carissa Loft A🏝️ A well-designed home offering comfortable spaces to relax, reconnect & experience all that AMI has to offer! Step inside to discover a private lower level retreat featuring a queen bed, sofa, TV and game table. Upstairs you'll find the fully stocked kitchen, inviting family room, 2-bedrooms & 2-full baths. The private outdoor oasis features a heated/cooled cocktail pool. 🚙Park the car & let the island adventures begin! The 6-person golf cart is complimentary with your stay!

4.96 out of 5 average rating, 212 reviews

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.

Home in Bradenton beach

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 two-story beach house features a wooden staircase leading to a wrap-around balcony. Lush tropical landscaping surrounds the entrance, and several palm trees are visible. Large windows allow natural light to fill the home, enhancing the inviting facade.

4.98 out of 5 average rating, 41 reviews

Anna Maria Beach House

Come stay at our beautiful beach house in Anna Maria, Florida! Located just a few hundred feet from the beach on Maple Avenue, you can easily walk to the Gulf for a day of family fun on the white sand beaches. The house is also walking or biking distance to center of Anna Maria with great restaurants. Please Note: We want to respect our neighbors. This is not a party house. We have a six person and three car maximum. Please reach out for exceptions. If not, you will be asked to leave.

4.95 out of 5 average rating, 20 reviews

Hidden Haven / Private Pool & Hot Tub

Your dream bayside escape at this charming single-story haven, just a heartbeat away from the pristine shores of Anna Maria Island. Featuring 4 inviting bedrooms and 2 stylish baths, indulge in the luxury of a private pool nestled among vibrant tropical foliage. Sip your morning coffee or toast to sunset cocktails poolside, wander to the sparkling Gulf, discover the delightful shops and eateries in Holmes Beach. This oasis is perfect for sun-kissed relaxation and exciting island escapades!

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, 111 reviews

Salty Harbor AMI pool retreat near the Beach

Charming Salty 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: -Ask us if your dates don't fit our calendar! -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

4.98 out of 5 average rating, 125 reviews

Home in Bradenton Beach

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

5.0 out of 5 average rating, 11 reviews

NEW! w/ Pool - The Pearl Unit 2 on AMI

The Pearl (Unit 2) is a newly renovated oasis in the heart of Holmes Beach on Anna Maria Island. Just a 3–5 minute walk to the beach, this sunny AMI duplex home has everything — sparkling saltwater pool, fresh interiors, no stairs, beach gear, and parrots that may say hi on your morning walk! Centrally located and steps away from the AMI trolley to whisk you around the island! Relax, explore, and live your best island life. *pool is shared with one other unit in the duplex home*

Superhost

5.0 out of 5 average rating, 5 reviews

NEW! Steps to Beach, Hot Tub, Pool, Kid Friendly

6-minute stroll to the private beach, heated pool, bubbling spa & ping-pong fun—perfect for families seeking sunshine! 3 bedrooms - 2 kings, 2 fulls +1 trundle twin (sleeps 6) Chef-ready kitchen + outdoor grill Beach chairs, beach umbrellas, + beach wagons Pack ’n play, stroller + high chair included Explore nearby cafés, boutiques and coastal bike paths, then unwind under the stars by the pool. Ready for a worry-free getaway? Click “Reserve” before your dates disappear!

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.

4.96 out of 5 average rating, 158 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 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, 163 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!

An outdoor dining area is set with a glass table and six blue chairs, shaded by a blue umbrella. In the background, a swimming pool with surrounding tropical plants invites relaxation, while a spa is visible nearby, offering a serene ambiance.

4.82 out of 5 average rating, 104 reviews

Private pool, only two blocks .3 miles from beach!

Just two blocks away from the beautiful white sands of Holmes Beach. Restaurants & night life even closer. Swimming pool and spa are inviting for both romantic getaways as well as families. You will have access to the entire beautiful two story townhouse. The property has a shared wall, but all space is private and quiet. The outdoors are separated and private as well. Plenty of parking, sun, & fun. New mattresses, new couch, and other furniture.

Popular amenities for house rentals in Holmes Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.88 out of 5 average rating, 129 reviews

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

A private pool is surrounded by tropical landscaping, featuring a clear blue water surface that reflects soft lighting. Several lounge chairs are positioned nearby, providing relaxation space under the palm trees. The serene area is perfect for unwinding after a day at the beach.

4.96 out of 5 average rating, 107 reviews

Beach House w/Private Pool & Spa

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.

4.9 out of 5 average rating, 73 reviews

TOES IN THE SAND!

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.

4.95 out of 5 average rating, 22 reviews

1 Block to Beach ~ 3BR Coastal Retreat with Pool

5.0 out of 5 average rating, 21 reviews

Luxury Escape, Pool, Beach, Essentials & Fun!

The exterior of the villa showcases a two-story structure featuring a light-colored façade. Lush greenery surrounds the property, complemented by a paved driveway. The spacious balconies are adorned with seating, inviting relaxation among the tropical landscaping. Two garage doors provide convenient parking.

4.94 out of 5 average rating, 47 reviews

5 min Walk to Beach & Dining in a Private Street

4.98 out of 5 average rating, 58 reviews

Golf Cart Included | 3 BR | Beach One Block Away

5.0 out of 5 average rating, 6 reviews

Island Vibe 5

Weekly house rentals

The exterior of the historic home is shown, featuring a wide wrap-around porch adorned with American flags. Several rocking chairs provide seating, surrounded by lush greenery and a gravel pathway leading to the entrance. Sunlight casts a warm glow on the porch area.

4.87 out of 5 average rating, 53 reviews

Welcome to our historic Florida beach HOME

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.

5.0 out of 5 average rating, 29 reviews

Eileen’s house- steps to the beach.

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.

4.85 out of 5 average rating, 20 reviews

Reese's Beach Retreat

5.0 out of 5 average rating, 15 reviews

The Pink House - Short Walk to the Beach

4.93 out of 5 average rating, 41 reviews

Kiwi Cabana by Beach Boutique 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.

5.0 out of 5 average rating, 47 reviews

Shell House: Seconds to the Beach! Clean & Cozy

Superhost

4.89 out of 5 average rating, 19 reviews

Zen Beach Cottage: Beautiful ground level home

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, 33 reviews

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

Private house rentals

5.0 out of 5 average rating, 32 reviews

New! Heated Pool • Shopping • Pine Ave • Beaches!

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.

4.85 out of 5 average rating, 61 reviews

Cozy Cottage - POOL HOME! 3/3

5.0 out of 5 average rating, 19 reviews

Wonderful 3/2 close to beach! Heated pool!

5.0 out of 5 average rating, 11 reviews

Beach House Steps from the Water-Anna Maria Island

4.89 out of 5 average rating, 47 reviews

Ocean72 | Heated Pool & Spa | 2BR Near Beach

A spacious living area features large windows offering water views and ample natural light. A comfortable sectional sofa is arranged around a round coffee table, and a cozy armchair is positioned nearby. Light-colored flooring complements the open layout, creating a bright and airy atmosphere.

5.0 out of 5 average rating, 29 reviews

Villa Mar- 2BD Waterfront Home in Holmes Beach, FL

5.0 out of 5 average rating, 6 reviews

Seaside Villa a waterfront in Paradise

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.