Luxury rentals in Anna Maria Island

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Top-rated luxury holiday rentals in Anna Maria Island

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Luxe

Home in Anna Maria

4.71 out of 5 average rating, 7 reviews

Pool, Rooftop Putting green, Golf cart, and Bikes!

Palmetto Paradise by AMI Locals Home in Anna Maria, Florida Welcome to Palmetto Paradise, a gorgeous vacation home just two houses from the stunning Gulf of Mexico beaches with four bedrooms and four and a half baths. You will be amazed by this home’s amenities, which include an incredible two-level rooftop deck with beach views, a putting green, a state-of-the-art outdoor kitchen, and a sparkling pool and spa. his home is part of our Exclusive AMI Collection of homes. These luxury properties

Luxe

Home in Tampa

5 out of 5 average rating, 11 reviews

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.

Luxe

Home in Sarasota

5 out of 5 average rating, 8 reviews

Sunset Gazers Paradise - Resort Pool - Mini Golf

Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation experience! Endless Horizon is the most accurate description for this luxury Siesta Key vacation rental that is located directly on the Gulf of Mexico and provides some of the most remarkable views of the Gulf, Big Pass, Lido Key, and greater Siesta Key and Sarasota areas! This amazing home is a casual bike ride or walk to the world-famous Siesta Key Beach and Siesta Key ...

Luxe

Home in Siesta Key

5 out of 5 average rating, 6 reviews

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.

Luxe

Home in Anna Maria

Lap of Luxury by Duncan Real Estate

Welcome to Lap of Luxury! This home is new as of 2022 and has been meticulously built and designed to create a space for full relaxation. Lap of Luxury is only 150 steps from the white sand beaches of the Gulf of Mexico with beautiful views from every floor. It features 4 bedrooms and 5 and a half baths and is just a short stroll away from the historic shopping area along Pine Ave and the famous Bean Point beach area. Step through the zen inspired courtyard area to the main entrance.

Luxe

Home in Sarasota

4.94 out of 5 average rating, 17 reviews

Lagoon Pool/Slide/Spa - Beach Volleyball/Ping Pong

Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation experience! Looking for your Lost Shaker of Salt? Well, you've found it in this luxury rental home on Siesta Key that pays homage to the late, great Jimmy Buffet and the theme behind his music - paradise, good vibes, and of course great cocktails with better friends! And what better house than one in the South Siesta Village entertainment district?

Luxe

Home in Sarasota

4.91 out of 5 average rating, 11 reviews

60ft. Water Slide - Golf Simulator - Mini Golf

Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation experience! Located in the heart of South Siesta Key Village! You are literally steps to all South Siesta's restaurants, entertainment, shopping, markets, marina, and much more! This super fun entertainment district is literally at the end of your street, steps away, and it has something for everyone, which is why it's a guest favorite!

Luxe

Home in Siesta Key

5 out of 5 average rating, 6 reviews

New luxury home with rooftop deck - Seashell Esta

Seashell Esta by Siesta Key Luxury Rental Properties Home in Siesta Key, FL 34242 Welcome to Seashell Esta, a luxurious new home located in Siesta Key. With seven bedrooms, seven and a half bathrooms, and three stories of top-notch amenities, you are in for a truly remarkable stay. From private balconies to the rooftop deck, you will be treated to unparalleled views of the Gulf, breathtaking sunsets and an impressive resort-style backyard.

Luxe

Home in Bradenton Beach

Elevator, Endless Summer by SeaBreeze Vacation

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER 4/27/23! All Drivers must be over the age of 21. Driver’s must provide valid US Driver’s License and US Vehicle Insurance. Endless Summer is the latest addition to SeaBreeze Vacation's portfolio. Pristine, newly constructed home features 7 beds/6 baths, an elevator, fantastic pool & spa, an EV Charger, and is just a 4-minute stroll from the shoreline

Luxe

Home in Sarasota

5 out of 5 average rating, 3 reviews

2440 Arlington Park Luxury House

Welcome to 2440 Floyd Street, a stunning, modern retreat in the heart of Sarasota. This spacious 6-bedroom, 4.5-bathroom home offers luxury, comfort, and privacy, making it the perfect getaway for families, groups, and corporate travelers. With a heated pool, private rooftop terrace, and a detached guest house, this home offers a true resort-style experience just minutes from Siesta Key Beach, Lido Key, and downtown Sarasota.

Luxe

Home in Sarasota

5 out of 5 average rating, 8 reviews

Sport Court Feat. Pickleball - Theatre Room - Pool

Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation experience! This spectacular luxury rental home is literally steps to all the South Siesta Village restaurants, entertainment, shopping, markets, marina, and much more! This super fun entertainment district is literally at the end of your street, just steps away, and it is a guest favorite!

Luxe

Home in Sarasota

5 out of 5 average rating, 7 reviews

#1 Home on Lido Key - Steps to Beach & St. Armands

Per City of Sarasota’s Rental Ordinance - This property must be rented for a minimum of 7 nights. If the travel dates you are looking for don’t appear to be available, please contact our reservations team directly and we will see if we can accommodate your request at your property of choice, or another comparable home in our portfolio.