Vacation rentals with a hot tub in Holmes 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.

Stunning beach house with heated pool and hot tub!

Welcome to The Colony, a stunning vacation rental on Anna Maria Island, designed to capture the essence of Palm Beach living. This spacious 4-bedroom, 4.5-bathroom house features elegant decor and modern amenities. Step outside to discover a beautiful backyard oasis, complete with a large pool, hot tub, and a well-appointed patio that invites relaxation. Just a 5 minute walk to the pristine beaches of AMI, The Colony is perfectly situated in charming Holmes Beach for an unforgettable getaway.

Payton's Place | Private Heated Saltwater Pool/Spa

Slow down, settle in, and soak up the island pace of life. Your family will be close to everything when you stay at this centrally located private home — just a short stroll to local restaurants, charming shops, and the free trolley stop at the end of the street by the library. The white sand beaches and turquoise Gulf waters are only a 7-minute walk away. Spend your mornings at the beach, your afternoons by the heated saltwater pool, and your evenings under the stars in your private spa.

Twin Tides, Pool Spa, Minigolf, Golfcart, Sleeps14

Discover the charm of island living in our newly opened island retreat, boasting a sprawling 3,600 square feet of living space. Be enveloped in the comfort and convenience it offers, ideal for family vacations or groups. Our home is managed by Beach Life Vacations on the stunning Anna Maria Island. We understand the importance of flexibility in these unpredictable times, so feel free to reach out and we'll strive to cater to your travel plans. This island paradise awaits!

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.

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

Coccoloba by Duncan Real Estate

Welcome to Coccoloba! This beautiful single-family home is located across from the sugar sand beaches in Holmes Beach. You enter the living room that features a large TV for great family entertainment. There is also a small table with chairs for a morning coffee or a cocktail before dinner or just hanging out with a good read. The galley style kitchen with a breakfast island is close by. This area has a large dining table with seating for six.

White Pearl - Pool/Rooftop/Mini Golf!

Luxury island retreat featuring 4 bedrooms plus an office with sleeper sofa, private pool, spa, putting green, rooftop deck, and multiple balconies. Enjoy a chef’s kitchen with premium Thermador appliances, spacious living areas, outdoor TV, dining for eight, and resort-style amenities. Beach gear included: 6 chairs, wagon, umbrella, and sand toys. Perfect for families and groups seeking a relaxing coastal escape! 🌴🏖️☀️

Waterfront Pool Home Steps to Beach

Escape to our waterfront oasis on Anna Maria Island! This bright, updated home features a private heated pool, hot tub, and dock. Perfect for families, it's just a 5-minute walk to the world-renowned Gulf beaches. Enjoy stunning sunrises, a dedicated workspace, and modern coastal decor. Explore the island with ease via the free trolley. Your perfect getaway awaits!

Beachy Blue by Beach Boutique Rentals

*Features include* * Private tropical yard with heated pool and spa * 4 bedrooms w/ 2 king master suites * 4 full bathrooms * Patio dining for 8 * Heated pool with spa * Game room with basketball * Family friendly features - bunk beds, pack n'play * Walk to popular shopping and dining destinations * Beach chairs, umbrella, and cart * Super close to the beach!

Las Palmas Beach Rentals unit 2

Ground floor; limited beach view . Steps to the white sandy beach. Free parking to registered guest. Furnished rooms, full size kitchen, linens provided. Free trolley stop on the block. GREAT LOCATION! Shopping and restaurants short walking distance. Check out our guidebook for additional island tips. Once booked it will be in your itinerary.