House holiday rentals in Holmes Beach

New Golf cart + 4bd/2b+ pool/shower/deck

Urban Oasis too is a privately owned home on Anna Maria Island. It has 3 bd 2 bth plus bonus room with a large pool, 10,000 sq foot yard, two large decks, outdoor bar and dining space AND a brand new 2024, 6 seater electric golf cart included! This private home features coastal hues, driftwood accents and comfortable furniture to enjoy your vacation. You will have premium linen service including all towels and linens changed with each stay. You can also check out our original Urban Oasis on AMI!

1 Block to Beach ~ 3BR Coastal Retreat with Pool

🏖️Welcome to “Beach Therapy”, a serene 3-bedroom, 2 full bath coastal home just one block from the beach. This peaceful retreat offers a bright, open living space with a screened deck, perfect for relaxing in the coastal breeze. Enjoy a gas grill for outdoor meals, fast Wi-Fi, smart TVs, and all the beach essentials you need. With access to a shared pool and located in a quiet neighborhood, it's an ideal getaway for families and friends looking to unwind and enjoy a tranquil, beachside escape.

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

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!

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.

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!

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

NEW! w/ Pool - The Pearl Unit 1 on AMI

The Pearl (Unit 1) 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*

Heliconia House by Duncan Real Estate

Welcome to Heliconia House! This remodeled and furnished two bedroom and two bathroom duplex has its own private heated pool in the heart of Holmes Beach. Bring your furry family member too! Guests will enjoy a well-equipped kitchen perfect for preparing a gourmet meal or cook outdoors on the gas grill. The living area is spacious, with plenty of seating for family and friends to take in a movie on the flat panel HDTV. There is a breakfast island with seating for 4.

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!

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.

Amazing location and location! One min. to Beach!

A charming 2BR/2BA beach house just a stone’s throw from the sparkling shores of Anna Maria Island. Walk to the beach, Publix, or Skinny’s Burger restaurant in minutes. Relax by the private pool or unwind in a lush tropical backyard filled with palms and coastal breezes. Bright, beachy interiors, a fully equipped kitchen, and cozy living spaces make this the perfect island escape for families, couples, or weekend getaways.