Holiday rentals with a hot tub in Anna Maria

Gulf front best sunset views, Anna Maria Island

You only have to go down 14 stairs from your second-floor beachfront condo to have your toes in the powder soft sand. A queen size bed with a soft mattress in the bedroom and a queen size pullout couch in the living room. Full kitchen in the unit and laundry available downstairs. Cable and high-speed internet included. One assigned parking spot. Enjoy the sunset from your balcony as it sinks into the Gulf. Perfect for a romantic couple getaway or bring the kids for a fun stay at the 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.

Heated Pool, Hot Tub, Game Room, Steps to Beach!

Welcome to Island Dreams, the ultimate peaceful escape just 4 min walk from Anna Maria Island's stunning beaches. This fully renovated three-bedroom, three-bath beach house features a Zen-inspired backyard oasis, a private cocktail pool, and a game room! Walk to shops, restaurants, and the trolley stop! Island Dreams offers the perfect blend of relaxation, location, and indoor and outdoor fun! NOTE: Holmes Beach has a 7-day rental minimum. Check in / Check out days are on Saturdays.

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach

You asked, we delivered. Inspired by our Top 1% listing and consistent 5⭐ stays at “The Tiny Oasis”, Haus De Noir is a moody, boutique 3BR/3BA retreat with Plunge Pool, Hot Tub, Sauna, Outdoor Cinema and More! Slip into the Midnight Kafana, your own after-hours Hideaway Bar with Karaoke, Lights, and Late-Night energy. Fully stocked with everything you need and then some! Family-Owned and Managed! We don’t just host we LOVE what we do! Just 10 mins to Indian Rocks & Madeira Beach🏝️.

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

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.

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.

Oceanfront Condo for Beach Lovers

Located in Anna Maria Island Club - Our home away from home. Wonderful Panoramic View of Gulf of Mexico. 2 bedroom, 2 bath, heated pool, hot tub. Balcony overlooking the Gulf. Near to restaurants and shops. The heated pool and the hot tub is renovated. The elevator is working and we have a new security system. We had no hurricane this season . Everything is better than before the hurricanes last year.

Bean Point Bliss by Duncan Real Estate

Welcome to Bean Point Bliss! This stunning 3-bedroom, 2-bathroom pool home has plenty of room for the whole family. Bean Point Bliss is an elegant Island home with living space all on one level. A total of 6 people will stay here very comfortably. The additional area on the ground-level (not under a/c) is featuring a ping pong table, TV, and a seating spot which opens up to the back yard pool oasis.

Ocean72 | Heated Pool & Spa | 2BR Near Beach

Welcome to your island escape at Ocean72 in Holmes Beach! Just a short walk to sugar-white beaches, this coastal retreat features a private heated pool & spa, lush tropical landscaping, and seamless indoor-outdoor living. Enjoy a fully stocked kitchen, plush beds, and beach gear. Guests also have the option to add a private golf cart for easy island exploring and beach trips.

NEW! Blue Pearl~Heated Pool/Spa~Walkable Pine Ave!

Blue Pearl is a 4BR/3BA island retreat 🌊 on Anna Maria Island’s north end, just 7 minutes to the beach 🏖️ and 3 minutes to Pine Ave 🛍️. This spacious home features a private pool & spa 🏊, lush backyard, BBQ grill 🍔, beach gear, and a detached guest suite for added privacy. Pet-friendly 🐾 and perfect for families or groups seeking comfort, space, and island charm.

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!