Luxury rentals in Anna Maria Island

Only 10 Min to UTC Heated Pool King Adjustable Bed

Our 2-bd 2.5 bath townhome is nestled just 10 min to Siesta Key Beach, Grocery Stores, Restaurant's, Medical Centers & Golf Courses--ideal for snowbirds looking to unwind in style for a carefree & peaceful stay. The primary suite features a plush king bed with adjustable bedframe, ensuite bath & a towel warmer + a custom closet. Whip up a culinary masterpiece in our kitchen with a Breville Airfryer & Samsung appliances. Enjoy the evening breeze on the lanai or relax by the heated community pool.

Showstopper Beach Home Pool Spa Waterfall Elevator

Welcome to the Kingdom on Hyde, the crowning jewel of Arlington Park homes & a vacation lover's dream. Featuring 4 bedrooms & 6 baths spread over nearly 4000 sq ft w/ 20ft soaring ceilings. This jewel box features a heated pool & spa with dramatic 8ft waterfall feature, Thermador Appliances, commercial grade elevator, custom imported tile & finishes & 2-story living amongst the Live Oaks. Perfectly situated a stone's throw from Arlington Park & a short drive to Siesta Beach & Downtown Sarasota!

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.

Lido Luxe Estate: Rental with Pool + Rooftop Deck

Lido Luxe Estate by Lido Key Vacations Vacation Rental License #VR25-00081 Minimum stay duration of 7 days/nights Experience unmatched luxury at Lido Luxe Estate, Sarasota's finest island retreat located in the prestigious Lido Key! This beautifully appointed six-bedroom, six and a half bath home offers a perfect combination of elegance, privacy, and entertainment. Located just a short six-minute walk from pristine Gulf beaches and the high-end shops and restaurants of Lido Key’s renowned

Rooftop Views! Pool, Spa and Game Room!

Love Me Blue by Exclusive Vacations 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 with a spa, and exclusive touches like a

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.

Island home with Pool and swim-up bar! Best

The Blue Crab by Anna Maria Vacations Home in Holmes Beach, Florida 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

#1 Rooftop Deck w/ Gulf Views - Steps to Beach

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

Private Ultra-Luxury 10 Bedroom | 14 Bath Mansion

Welcome to THE Estate Tampa Mansion! ✦10 master ensuites ✦14 Bathrooms ✦20,000 sf of space ✦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 10 years of age.

Luxury, Downtown, Rooftop Views, Top Beaches

A spacious modern 4-story luxury townhome in the heart of Sarasota. Within walking distance to Downtown’s top restaurants, shopping, weekend farmer's markets, nightlife, live music, and more! Perfect for a luxury retreat or the business traveler looking for an elevated experience. Contemporary decor throughout the open floor plan and a private rooftop with an outdoor kitchen and gorgeous views of the city.