Luxury rentals in Anna Maria

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Top-rated luxury holiday rentals in Anna Maria

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Luxe
Villa in Sunset Park
5 out of 5 average rating, 6 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
Townhouse in Tampa

Luxury Hyde Park Artists Home - Close to UT

Welcome to The Strata Barn, located directly between Hyde Park Village and the University of Tampa! This breathtaking townhome has been outfitted for those who like to travel in style. Located just 3 blocks from charming Hyde Park Village, you are walking distance to outdoor shopping, amazing restaurants, and vibrant bars that Hyde Park is known for. This professionally decorated home offers 2 bedrooms, 2.5 bathrooms, with 1 King bed, 2 twins, and a sleeper sofa, making this suitable for up to

Luxe
The outdoor area showcases a large, heated pool surrounded by well-manicured grass. A modern home with multiple balconies and expansive glass doors provides a view of the gathering spaces. Lounge chairs and tables offer options for relaxation and socializing.
Home in Lido Key
5 out of 5 average rating, 3 reviews

Lido Luxe Estate: Rental with Pool & Rooftop Deck

Lido Luxe Estate by Lido Key Vacations 540 S Polk Dr, Sarasota, Florida Vacation Rental License #VR25-00081 Minimum stay duration of 7 days/nights Welcome to Lido Luxe Estates, Sarasota’s Hidden Gem in Lido Key! This beautifully appointed 6-bedroom, 6.5 bathroom home offers the perfect retreat for families, groups and friends seeking a luxurious beach escape. Ideally situated just a short walk from the pristine Gulf beaches and the upscale shops and restaurants of St. Armands Circle, Lido

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, 5 reviews

Rooftop Views! Pool, Spa and Game Room!

Love Me Blue by Exclusive Vacations 792 Jacaranda Rd, Anna Maria, FL 34216 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

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, 23 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
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 7606 Marina Drive, Holmes Beach, FL 34217 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

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
Home in Sarasota
4.92 out of 5 average rating, 13 reviews

60ft. Water Slide - Golf Simulator - Mini Golf

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.

Luxe
The exterior showcases a modern three-story house with multiple large glass doors and windows. Balcony seating is visible on the middle and top levels, complemented by two umbrellas for shade. Lush landscaping surrounds the property, providing a tropical feel.
Home in Lido Key
5 out of 5 average rating, 4 reviews

Steps to Beach - St. Armands - Resort Pool & Slide

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.

Luxe
An aerial view of a modern coastal home highlights its spacious rooftop deck with ample seating. Surrounding palm trees and a backdrop of the Gulf of Mexico contribute to a serene coastal setting under a bright blue sky.
Home in Lido Key
5 out of 5 average rating, 5 reviews

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

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.

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, 7 reviews

Gulf Views. Walk to St Armands+Beach. Pool+Slide

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.

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.

Popular amenities for Anna Maria luxury holiday rentals

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