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

4.79 out of 5 average rating, 14 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

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

A three-story coastal building stands prominently with a two-tone facade. Large windows are adorned with blue shutters, allowing ample natural light. Palm trees are visible nearby, and a well-maintained garden outlines the entrance, contributing to the inviting coastal ambiance of the property.

Home in Clearwater Beach

4.87 out of 5 average rating, 23 reviews

Akoya 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 or spa, or strolling along the powder white sands of Clearwater Beach, "Akoya House" ensures that your vacation dreams become a reality.

Luxe

Villa in Sunset Park

5 out of 5 average rating, 5 reviews

10 Bdrm / 14 Bath Mansion - S. Tampa | Pool | Spa

Welcome to THE Estate Tampa - the area's newest & hottest vacation rental. Your chance to book the entire 20,000 sq ft mansion! ✦10 master ensuites ✦14 Bathrooms ✦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 12 years of age. Contact

Luxe

Home in Dana Shores

5 out of 5 average rating, 22 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

A modern home features a private pool surrounded by lush green artificial grass. Sunlight reflects off the clear water, with spacious lounging areas visible under the elevated deck. Palm trees frame the scene, adding a tropical feel to the inviting outdoor space.

Home in Anna Maria

5 out of 5 average rating, 4 reviews

Rooftop Views! Pool, Spa and Game Room!

Love Me Blue by AMI Locals 792 Jacaranda Rd, Anna Maria, FL 34216 Welcome to Love Me Blue, a brand-new four bedroom, four and a half bath luxury retreat 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 spa, and exclusive touches like a golf cart and luxury

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, 14 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 Lido Key

4.86 out of 5 average rating, 7 reviews

New Home with Pool, Spa, Waterslide - Seascape

Seascape by Lido Key Vacations Sarasota FL 34236 VR24-00004 Welcome to Seascape, a stunning vacation home boasting eight spacious bedrooms and eight-and-a-half luxurious bathrooms. With a gorgeous private pool, spa, and waterslide, you'll be living in paradise! Plus, the rooftop deck offers incredible views, and it's only a block away from Lido Key Beach, where you can catch breathtaking sunsets. This vacation home is perfect for families and large groups seeking a memorable beach

Luxe

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 fire pit.

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

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

An aerial view captures the coastal estate shimmering at dusk, surrounded by lush tropical landscaping. The beachfront property features soft sandy shores along the gentle waves, and a volleyball court is visible on the manicured lawn, providing a sense of outdoor recreation.

Home in Siesta Key

5 out of 5 average rating, 3 reviews

Chateau de la Siesta | Beachfront, Pool, Lanai Bar

Exclusive Amenities Include: • Private Beachfront & Sunset Views • Lagoon Pool, Heated Spa & Tiki Bar • Gulf-Front Firepit & Volleyball Court • Hammock Between Beachfront Palms • Gourmet Kitchen & Spacious Living Areas • 4 Gulf-View Bedroom Suites w/ Balconies • Tropical Landscaping • Starter Packs of Essentials for Kitchen and Bath • Beach Towels, Chairs, Cooler & Caddy Provided • Enhanced Cleaning by our CottageClean Team