Home rentals with a pool near Anna Maria Island

Beach Escape & Pool, steps to Beach & restaurants

One block from beautiful beach & waterfront dining. Newly renovated Villa in quaint quiet condo building close to everything on Anna Maria Island. Pickleball across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. *Min. renter age 25. Two minute walk to beach, trendy Bridge Street shops, marina, restaurants, bars, boat tours, mini golf and more. Brand new beds, furniture & appliances. Kitchen has everything you need. Beach supplies in hall closet.

Steps to the beach! Condo with pool at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

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.

Breezy Harbor AMI pool retreat near the Beach

Charming Breezy Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -We typically have shorter stays available, just ask! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

Heated Pool, Elevator, Dock, Waterfront, Fire Pit

Escape to The Blue Ark, a unique 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 private pool & spa, 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, 8 beds and 4.5 bathrooms.

Short Stroll to the Surf! ~ Make Memories on AMI

Nestled in a charming, quiet community of just 8 units, this beautifully updated beach condo offers the perfect blend of relaxation and convenience. The condo is just a short stroll (about 150 steps!) to the pristine white sand beach, where you can soak up the sun and enjoy the coastal views. Wonderful family getaway or couples escape. Private, covered 2 car parking. Laundry in unit. Beach wagon, chairs and gear available. A hidden gem close to everything you need for a relaxing island stay.

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Oceanfront: Open Thusday, $203/nt!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

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

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

Beachfront Paradise! Ground level with Heated pool

Gulf-front getaway with unbeatable beach access—step out your back door and right onto the sand! Enjoy a king bed, queen sleeper, fully stocked kitchen, in-unit washer/dryer, and professional linen service. Beach towels, two chairs, and an umbrella are included. Relax or grill by the shared heated pool and soak in the stunning Gulf views. Everything you need for the perfect beach escape—just bring your sunscreen and unwind!

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.