Luxury rentals in Anna Maria

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Top-rated luxury vacation rentals in Anna Maria

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Luxe

Home in Anna Maria

5 out of 5 average rating, 6 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

An open patio features a large outdoor dining table and a ping-pong table, with views of the Gulf and palm trees. The sky is adorned with soft hues of orange and yellow during sunset, creating a serene atmosphere. The seaside landscape is visible beyond the well-maintained lawn.

Home in Sarasota

5 out of 5 average rating, 4 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

A serene bedroom features a spacious bed adorned with soft linens. A dresser with a coastal-themed artwork is situated against the wall. Natural light floods the room, highlighting a flat-screen TV and a woven laundry basket in the corner.

Home in Siesta Key

New place to stay

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

A sparkling lagoon-style pool is surrounded by tropical palm trees, creating a serene and inviting outdoor retreat. The pool features a winding shape with beach entry, sun shelves, and cascading greenery, enhancing the relaxation space for guests.

Home in Sarasota

4.94 out of 5 average rating, 16 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

The outdoor space features a landscaped area with a heated saltwater pool and spa, accompanied by a 60-foot waterslide. Smooth putting greens and lounge chairs are situated around the pool, enhanced by lush tropical plants and the inviting glow of dusk.

Home in Sarasota

4.9 out of 5 average rating, 10 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

An aerial view showcases a luxury home featuring a large pool and a multi-sport court. The outdoor area is surrounded by palm trees, with loungers positioned by the pool and seating areas located on the rooftop deck. The peaceful environment is complemented by well-maintained landscaping.

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

A stunning view showcases a saltwater pool and spa surrounded by landscaped greenery and lounge chairs. The scene is framed by palm trees and overlooks a serene bayou with waterfront homes under a vibrant sunset sky filled with colorful clouds.

Home in Lido Key

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.