Luxury rentals in Anna Maria

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Top-rated luxury vacation rentals in Anna Maria

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Luxe

An open living area is highlighted by a dark leather sofa and a stylish armchair, with unique artwork adorning the walls. A modern light fixture hangs above the space, while a small staircase leads to upper levels, featuring wooden steps with a sleek metal railing.

Home in Channel District

4.73 out of 5 average rating, 11 reviews

Downtown Tampa - The Luxe Loft in Channelside

Want the feel of a private hotel without having to deal with the inconveniences? No key fobs or gate codes or confusing directions on how to get to your home away from home! Just pull into your PERSONAL ATTACHED GARAGE to access Tampa’s 1st & only Luxe property! Come stay @ Tampa's Luxe Loft in Channelside, you’ll be steps away from the best dining, nightlife & waterfront experiences. Catch a show at the Amalie Arena, stroll along the Riverwalk, explore the Florida Aquarium, or enjoy nightlife!

Luxe

The exterior of a modern three-story home is highlighted, featuring multiple large windows with white shutters. A walkway leads to the entrance, which is framed by greenery. The surrounding area shows a well-maintained landscape with evenly spaced pavers.

Home in Clearwater Beach

4.92 out of 5 average rating, 12 reviews

Pearl House at The Gemma

Just steps away from the quartz white sand of Clearwater Beach sits a brand new collection of homes, "The Gemma." With spacious layouts, modern amenities & upscale furnishings "The Gemma" vacation homes provide a haven for travelers seeking the ultimate beachfront experience. Whether you're savoring your morning coffee on a private balcony, basking by the pool and spa, or strolling along the powder-white sands of Clearwater Beach, "Pearl House" ensures that your vacation dreams become a reality.

Luxe

The exterior of a coastal-style home is framed by lush tropical landscaping. Two palm trees and various shrubs surround the property, while the distinct architecture features a tower and a large covered porch. The garage doors have rustic wooden accents, adding charm to the overall design.

Home in Holmes Beach

5 out of 5 average rating, 5 reviews

Island home with Pool and swim-up bar! Best

The Blue Crab by AMI Locals Holmes Beach Vacation Rental VRC-000057 Welcome to The Blue Crab, a stunning island retreat just two 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 relaxation, recreation,

Luxe

An inviting outdoor space features a private pool surrounded by a well-maintained lawn and stylish pavers. Comfortable loungers are arranged for relaxation, while a shaded seating area is adjacent, offering a smart TV for entertainment. Lush greenery adds a sense of tranquility to the setting.

Home in Tampa

5 out of 5 average rating, 16 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

The multi-level vacation rental is illuminated under the evening sky, showcasing a shimmering heated pool with colorful lighting. Spacious balconies offer views across the exterior, while modern lounge chairs are positioned around the inviting pool area.

Home in Siesta Key

5 out of 5 average rating, 12 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

An aerial view showcases a modern two-story beach house surrounded by lush palm trees. Below, a private pool glistens, complemented by elegant lounge chairs along the poolside. The spacious balcony features outdoor seating, ideal for enjoying sun-splashed days.

Home in Anna Maria

5 out of 5 average rating, 4 reviews

Luxury home! Pool and Spa, Golf cart, and Bikes

Sweet Caroline by AMI Locals Home in Anna Maria, FL VR23-000009 Welcome to Sweet Caroline, a newly constructed four-bedroom and four-and-a-half bathroom home just one small block from the quartz-sanded Gulf of Mexico Beaches. This modern beach house is outfitted with every luxury amenity you can think of, from a rooftop deck that boasts sensational views, an elevator to take you from each floor to an impressive backyard with a private pool, in-ground spa, a putting green, and a fabulous,

Luxe

A private lagoon-shaped pool is surrounded by lush greenery and features two sun loungers. The pool area includes tiki umbrellas for shade and a deck with steps leading to the home, characterized by a charming blue exterior and large windows.

Home in Holmes Beach

5 out of 5 average rating, 3 reviews

Tiki By The Sea by Duncan Real Estate

Welcome to Tiki by the Sea! This beautiful, centrally located 5-bedroom, 3-bathroom pool home has 1,921 under A/C square feet of elevated living space and offers the best of Island vacationing. Up to ten guests will be accommodated very comfortably inside and out. From the quality quilts and linens on the beds, TVs in 4 of the 5 bedrooms and several fantastic outdoor areas nothing has been spared to provide a perfect beach getaway. HIGHLIGHTS 1921 sq. ft. Pool side Tiki bar

Luxe

A rooftop deck offers a spacious dining table surrounded by comfortable chairs, showcasing a view of the sparkling Gulf waters and coastal landscape. The area is enhanced by clear blue skies and distant clouds, providing a serene setting for outdoor meals.

Home in Holmes Beach

5 out of 5 average rating, 3 reviews

Seaside Haven by Duncan Real Estate

Seaside Haven is an elegant Island property that promises an unforgettable experience. The 4 bedroom and 3 1/2 bath pool home is located on the Avenues in Holmes Beach and just a short flipflop walk to the Gulf powdery white beaches. This house features tasteful coastal-themed dcor that prioritizes guest comfort. Its gourmet kitchen and open floor plan provide ample space for family gatherings, complemented by a functional and relaxing outdoor living area by the pool with a firepit.

Luxe

The exterior of a three-story vacation home is highlighted, showcasing large glass doors and multiple balconies. Lush greenery surrounds the property, while a rooftop deck can be seen, providing additional outdoor space. The driveway offers ample parking with two garage spaces visible.

Home in Lido Key

5 out of 5 average rating, 6 reviews

Gulf Views/Walk to St. Armands & Beach-Resort Pool

Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation experience! Per City of Sarasota's Rental Ordinance - This home must be rented for a minimum of 7 nights, and it has a max occupancy of 12 adults, *but children under 6 years of age do not count toward the City's max occupancy count. Vunique Vacations restricts the total occupancy of the home to 16 persons, including adults and children under 6 years of age.

Luxe

A private heated pool is surrounded by tropical landscaping and wooden decking. A Tiki Hut with bar seating and string lights enhances the space, while a waterfall feature adds tranquility to the area, creating a serene outdoor retreat.

Home in Holmes Beach

5 out of 5 average rating, 4 reviews

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.

Luxe

A spacious outdoor area is featured, showcasing a modern pool surrounded by comfortable lounge chairs. Lush greenery and palm trees enhance the setting, while a shaded patio area offers ample seating for dining and relaxation.

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

The modern exterior of the home features a clean white facade with large windows, providing natural light. A welcoming entrance is marked by stylish light fixtures and palm trees, while colorful landscaping enhances the overall curb appeal.

Home in Sarasota

5 out of 5 average rating, 4 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.