
Luxury rentals in Anna Maria
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Top-rated luxury holiday rentals in Anna Maria
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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

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

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

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

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.

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.

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

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.

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.

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.

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

Elegant 6BR Sarasota Home • Pool + Rooftop Views
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.
Popular amenities for Anna Maria luxury holiday rentals
Other great luxury holiday rentals in Anna Maria

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Beachfront Home with Pool, Golf Cart and Bikes!

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Luxury Home! Pool with Spa, Waterslide- Big Kahuna

Rooftop Deck, Pool, and Golf Cart at Deckadence
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- John's Pass
- Turtle Beach
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- Caspersen Beach
- Coquina Beach
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- Bean Point Beach
- Jannus Live
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- Tampa Palms Golf & Country Club
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- Gulfport Beach Recreation Area
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