Holiday rentals with a pool in Anna Maria

Green Jacaranda AMI Duplex B, 5 min walk to beach

Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

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.

Bermuda Bay Club 1427 by Duncan Real Estate

Welcome to the Bermuda Bay Club!This 3 bedroom/2.5 bath townhome is conveniently located in the Bermuda Bay Club complex with water views from the upstairs balcony. The Bermuda Bay Club community stretches from Gulf to Bay and is just a flip flop walk across the street to the white sandy beaches of Bradenton Beach. The complex has a large, heated pool to swim a few laps and a hot tub to relax. From the pool area, you can stroll down the mangrove lined boardwalk to the Bay where you can try ...

Anna Maria retreat house

Elevated home with all the amenities. Walking distance to the beach, chairs and towels provided. Relax in the backyard patio, including pool with waterfall . The shaded balcony overlooks the pool if you need to escape the sunshine. There’s a free trolley that runs all day in AMI if you don’t want to take the car out. The house is located across the street from Bimini Bay, enjoy a jog through these side streets in the morning. Local shops and restaurants that will not disappoint .

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, modern waterfront vacation home & patio

Located on Coquina Key South we have panoramic water views of bayou and beautiful sunset views. Only 5min to downtown St Pete and 15 min to Pass a Grille Beach. Boyd Hill Nature Preserve 5 min away- offers great hiking and biking. Gated resort-style complex with 2 pools, jacuzzi, pickle ball, tennis, fitness room, beach volleyball, shuffleboard court, basketball, Yacht Club with waterfront bar. You have access to every amenity, and they are all walking distance from our unit.

Bay Breeze Cottages #2

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

2 min walk to Gulf~3 king+bunk~pool+spa+golf+bikes

Experience an unforgettable vacation at Key Lime House! This chic Bahamian-inspired property sits at the coveted north end of Anna Maria. Every inch of space has been maximized with loads of indoor and outdoor amenities for guests of all ages. This is the special place you’ve been looking for to create memories that you’ll treasure forever! 🌴 2 min walk to Gulf beach access (7 houses away, see photos for path) 🌴 3 min bike ride to Bean Point or Pine Ave (bikes provided!)

Pool, Pets, Walk to Beach With Incredible Sunsets

Exclusive Amenities Include: • Located in the Heart of Anna Maria Island • Semi Private Heated Pool • Less Than a 5 Minute Walk to beach access; 0.2 miles to 72nd St. Public Beach Access • 3 Bedrooms, 2 Full Baths • 1 King Beds, 1 Queen Bed, 2 Twin Beds (Sleeps 6) with linens provided • Outdoor Balcony • Spacious Outdoor Patio • Barbecue Grill • Free WiFi & 4 TVs • Coffee Maker & Kitchen Essentials • Beach Towels, Chairs, & Caddy • Private Driveway Parking • Pets Stay Free

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.

Heated Pool, Steps to the Beach, Luxury Home

Welcome to your Anna Maria escape! Our 3-bed luxury home features a heated, private pool and is just minutes from the sugar-sand beach. • Spacious open-plan living & gourmet kitchen • Three serene bedrooms with premium linens • Outdoor lounge, grill & sun loungers • Fast Wi-Fi, smart TVs, washer & dryer • Beach chairs, and essentials • Superhost service ensures rapid replies and spotless cleanliness Book now and start making island memories!

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.