Luxury rentals in Anna Maria Island

Luxury Beachfront House in Anna Maria!

ANNA MARIA-LOCATED JUST STEPS AWAY FROM THE BEACH AND SHOPPING! This luxury house on the bay features sweeping views of the Bay, Passage Key, Beachfront, and Skyway Bridge. With 4 bedrooms and several entertainment areas this makes an amazing retreat for a family or group of friends that have luxury tastes while enjoying the relaxed atmosphere of Anna Maria. Features include a pool and spa with a putting green and rooftop deck! This is as luxurious as it gets with a short walk to downtown shops

Tampa Luxe Waterfront Private Pool, Hot Tub & More

Welcome to the first and only Airbnb Luxe property in Tampa and St. Pete—where every detail is curated for your comfort. This professionally designed waterfront home with direct Tampa Bay access features a private pool, hot tub, dock, chef’s kitchen, fast Wi-Fi, electric scooters, Weber Grill, fishing & beach gear for your adventures & more. Perfect for families or groups seeking relaxation and adventure. Ask us about private chef services and curated local experiences to elevate your stay.

Rooftop Views! Pool, Spa and Game Room!

Love Me Blue by Exclusive Vacations VR24-000043 Welcome to Love Me Blue, part of our Exclusive Collection. This luxury beach home offers four bedrooms, four and a half baths, located on the north end of Anna Maria Island! Just a three-minute walk to the serene Bean Point beach and one mile to the shops and restaurants of Pine Avenue, this stunning home combines resort-style amenities with elegant island living. Featuring a rooftop deck, private pool with a spa, and exclusive touches like a

Waterfront Home Private pool, elevator and dock

Luxury waterfront retreat w/pool, spa, boat ramp & dock! Elevator makes it perfect for multi‑generational family getaways. This brand-new home features airy open-concept living and 4 bedrooms (3 primary en-suites with King). Swim in the sparkling pool, soak in the spa, grill on the BBQ, and dine under the covered patio. Just minutes to Gulf beaches and local dining. Bring your boat and enjoy waterfront living from your own backyard oasis, where you can relax and watch manatees in the canal.

400ft to Beach, Ocean View, Pool, in the Village

Siesta Key Dream’s largest and most luxurious vacation rental, features four levels, totaling 6-bedrooms, 9-beds, & 6 full-bathrooms. Notable attributes include: a heated-pool, hot tub, 2-balconies, a roof-top sundeck, parking, a backyard and an elevator. With a premier location, beach access point #4 is 400 feet away, and the Siesta Key Village is one block away. In addition to a highly desired location, the unique property design allows beach and Gulf of Mexico views from multiple levels.

Island home with Pool and swim-up bar!

The Blue Crab by Anna Maria Vacations Home in Holmes Beach, Florida VRC-000057 Welcome to The Blue Crab, a stunning island retreat just three blocks from Holmes Beach! This luxurious four-bedroom, four and a half bath home boasts a tropically landscaped backyard featuring a private pool with a swim-up bar, fire pit, and hot tub. Surrounded by elegant, coastal farmhouse decor, the open layout offers plenty of space for family gatherings or friends’ getaways. Perfect for those seeking

Riverfront Oasis | Pool/Spa, Fire Pit & Games

Featured on Season 3 of the Emmy Award-winning TV series StayCation, Waterside Gardens is a meticulously crafted riverfront oasis in the heart of Tampa. “A++ this place was amazing. Best Airbnb I’ve ever stayed at. Would 100% stay here again” -Nick From the wall of windows overlooking palms and water to evenings spent watching the sunset from your own private beach, this home invites you to slow down and take in Tampa’s waterfront lifestyle. Every moment here feels extraordinary.

New Listing! Beachfront! 2 Masters w/Ocean Views!

The Diamond Star on Anna Maria Island, a beautifully remodeled beachfront home originally built by legendary pitcher Warren Spahn. Enjoy spectacular beachfront views, white sandy shores, and unforgettable sunsets. The house features two master suites, a living room, and a kitchen, all offering magnificent ocean views. Enjoy the private decks, direct beach access, beach gear including kayaks, paddleboards, and more. After a day in the sun, relax with a cocktail in the private pool.

Beachfront Luxury - Resort Pool - Steps to Village

Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway.

The Shady Mermaid by Duncan Real Estate

Welcome to The Shady Mermaid! A luxury ground-level vacation home just a 3-minute walk from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. Top of the range, fully equipped kitchen has ample counter space, gas cook top and oven, extra-large fridge/freezer and wine cooler making meal prep a breeze.

Gone Coastal on Elm - Short Walk to beach/Pine Ave

Gone Coastal on Elm – Your Luxe AMI Escape Awaits Welcome to Gone Coastal on Elm, a newly built five-bedroom, seven-bathroom island retreat designed for effortless relaxation and unforgettable memories. Ideally located on Elm Avenue, you’ll be just a short stroll from the soft white-sand Gulf beaches and the charming shops and eateries along Pine Avenue—one of the most coveted spots on Anna Maria Island! Managed by Doreste Properties

Private Ultra-Luxury 10 Bedroom | 14 Bath Mansion

Welcome to THE Estate Tampa Mansion! ✦10 master ensuites ✦14 Bathrooms ✦20,000 sf of space ✦saltwater pool | HUGE hot tub ✦professional gym | Ai personal trainer ✦chef's kitchen | commercial ice machine ✦lounge/bar areas ✦art gallery ✦billiard room ✦arcade | basketball | guitar hero | racing sims | air hockey | classic games ✦20-person dining table ✦This property is not suitable for children under 10 years of age.