Home rentals with a pool near Anna Maria Island

Waterfront, Heated Pool, Elevator, Fire Pit, Dock

Escape to The Blue Ark, a 3-story home inspired by Noah’s Ark. Families will love this peaceful retreat, blending luxury and comfort. Discover the island's only natural lagoon, boasting stunning views, manatee and occasional dolphin sightings! Unwind by the heated pool, fish from the dock, or take an easy 4-5 minute walk to the beach. End the day with a drink by the fire pit on the top deck, watching the sunset. The Blue Ark has an elevator, 3 bedrooms + extra sleep space, 8 beds and 4.5 baths.

Carissa B | Beachside Retreat | Golf Cart | Pool

Welcome to Carissa Loft B, your completely private half of a beachside duplex on AMI! The duplex is designed back-to-back, meaning you have your own private indoor/outdoor spaces, entrance & pool-No shared amenities! Loft B includes: 1pm CHECK IN, 3 beds, 2 baths, full kitchen, 2 living spaces, balcony, heated/cooled cocktail pool, & garage w/golf cart! Ideal for up to 6 guests. Need more space? You can book both sides of the duplex for larger groups while still enjoying separate living areas..

Green Jacaranda /Bean Point Beach 5 min walk/pool

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

100 yr Old Stone Home + Pool + 9 miles to beaches

Charming 100-Year-Old Restored Stone House with Italian Flair – Close to Beach & Downtown! Welcome to your dream getaway! This beautifully restored 100-year-old stone home blends old-world charm with modern luxury. Inspired by the elegance of Italy, this unique retreat is just minutes from the beach and vibrant downtown Bradenton. The home has abundant natural light and has 2 bedrooms, 2 half baths and a spacious yard! You will love the heated pool and outdoor firepit for year-round relaxing.

New Modern Longboat Key*5 Steps to Sand*Heatd Pool

Newly renovated (November 2025) modern first floor condo literally five steps away from the sand walking outside from the lanai. One bedroom /One bath King bed in Primary Queen sleeper sofa in living room Key code entrance Free parking Heated Swimming pool on site Free Beach loungers on the beach Paid laundry machines on site Mid Island next to everything WiFi, cable, free parking Usually 7 night minimum Bring your toothbrush and bathing suite and prepare to unwind and relax!!!!

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🏝️.

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 .

Beach Front Madeira Beach

PLEASE NOTE: SEVERAL UNITS UNDER CONSTRUCTION in the building. And our swimming pool is currently closed for renovations as well. Expected completion by May 31. Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away.

Siesta Key | Heated Pool | Sauna | Family & Pets

☞ Sauna, Fire-pit, BBQ (gas) ☞ Giant Outdoor Chess♟️ ☞ King & 2 Queen Beds ☞ Ample Parking (RV, Boat, etc) ☞ Fast WiFi 🛜 ☞ 4 Smart TVs (largest 85 inches) ☞ Gourmet Kitchen Main side ☞ Kitchenette on Guest side ☞ 2 Onsite washer + dryers ☞ 2 Outdoor Showers 》30 mins to airport 》2 mins to Siesta Key Beach Bike to America’s #1 beach, morning coffee runs, sunset rides, live music, ice cream, shops or any of the amazing restaurants in Siesta Key village.

Paradise Palms by Duncan Real Estate

Welcome to Paradise Palms! Casual and beachy this three-bedroom duplex with a private, heated pool and close proximity to the beach is the perfect choice for vacationers to relax and unwind when visiting Anna Maria Island. Your favorite dog is also invited for a small pet fee (50 lbs. max, please!). Paradise Palms is located two blocks from the powdery sand on Holmes Beach - so close you'll never miss a sunset.

Cabin 1 at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities and the free AMI trolley. You’ll love my place because of the location and the ambiance. Cabin 1 is part of Spinnakers Vacation Cottages located just steps to the sparkling Gulf. My place is good for couples, solo adventurers, families (with kids), and furry friends (dogs, for a small pet fee) Spa maintains same temperature as pool.

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴