Holiday rentals with a hot tub in Anna Maria

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.

Hot tub · Outdoor spaces · Parks

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!

Bathroom · Hot tub · Barbecue

Heated pool/Spa~Water Slide and Grotto! 9 Beds!

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.

Hot tub · Bathroom · Hospitality

Swim. Soak. Play. | Beaches | 5mi 2 IMG | Dine

Welcome to Villa Delfino—where summer days are filled with sunshine, beach adventures, and island exploration. When evening arrives, the villa transforms into a relaxing oasis with ambient lighting, outdoor gathering spaces, and the perfect atmosphere for creating lasting memories. Experience white-glove hospitality with a responsive local team, hands-on management, and detailed pre-arrival inspections. We're available throughout your stay to ensure a seamless, stress-free vacation.

Bathroom · Hot tub · Long stay

Beach House w/Private Pool & Spa

Adorable beach cottage on the north end of Anna Maria Island! The beach access trail to the beautiful beach is right by the house. This 3 bedroom 2 bathroom home is situated on a corner lot on a quiet street and is located just steps to the beaches of the Gulf of Mexico. Enjoy the private pool and spa, surrounded by tropical landscaping. Tons of beach gear included! It is located in a great area to explore by bike, ride to Pine Ave., Bayfront Park, the City Pier, etc....

Bathroom · Outdoor spaces · TV

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!

Outdoor spaces · Family · Getting around

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Beautifully renovated 5 bedroom home. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with string lights and heated pool and spa encompass this house. Master bedroom with walk-out to spa. Custom double walk-in shower in master suite. Family room with 86" television, decorative fireplace, and 15' ceiling. Roku TV’s in every bedroom. Outdoor propane grill. Beach chairs, umbrella, and cart. We welcome you to Casa Bella.

Hot tub · Outdoor spaces · Decor

Ocean Air Oasis-New Centrally Located AMI Luxury

Immerse yourself in coastal luxury at this exceptional 3-bedroom, 2.5-bathroom custom home, where opulent high-end finishes and stunning pecky cypress floors adorn every nook. Revel in the impeccable features, including Sub-Zero and Wolf appliances, marble countertops, Shaw’s sinks, and exquisite custom woodworking, all bathed in abundant natural light. This delightful space offers panoramic views of the lavish backyard, complete with a heated pool and spa.

Bathroom · Hot tub · Family

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.

Bathroom · Outdoor spaces · Check-in

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Bathroom · Outdoor spaces · Layout

Dock of the Bay by Duncan Real Estate

Welcome to Dock of the Bay!Located on the North end of Anna Maria, Dock of the Bay is a newly remodeled two- bedroom, three-bathroom vacation home directly on a canal with a private pool. This property has boat access to the intercoastal passing 2 low clearance bridges. Dock of the Bay is a direct walk to Bean Point which is one of the most picturesque parts of Anna Maria Island. HIGHLIGHTS • 2228 sq. ft.

Outdoor spaces · Bathroom · Biking

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!

Hot tub · Bathroom · Check-in