Holiday rentals in Anna Maria

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Anna Maria

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Home in Sarasota

4.88 out of 5 average rating, 147 reviews

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

Guest favourite

Home in Indian Rocks Beach

4.99 out of 5 average rating, 156 reviews

Luxe BeachHouseA Heated Pool, 2 min walk to Beach

Welcome to your home away from home. Sand,sun,and ocean breeze are waiting for you. Our modern Beach House is located 2 minutes walk from the beautiful and quite beach with direct beach access.Its a newly built three story house with nice backyard,heated pool,hot tub and beautiful rooftop. We have everything that you need for bigger groups of families to relax on your Beach vacation.Our Beach House is in a quite neighborhood and still walking distance from restaurants,bars and stor. BTR#2099

Guest favourite

Apartment in Sarasota

4.97 out of 5 average rating, 37 reviews

Siesta Key Village & Beach w pool & pet friendly

Location and value. No fighting traffic for hours to get to Siesta Key. Park the car and relax. The heart of Siesta Key village waits just outside the back door, and everything is within walking distance at this centrally located condo with a heated pool. The #1 voted beach in the USA and its powder soft sugar sand is an 7-minute walk. Paradise and serenity have been found. One of the few places that will allow your small dog to stay. Also one of the few you can rent for less than a week.

Guest favourite

Home in Sarasota

4.92 out of 5 average rating, 291 reviews

❤ Villa & Garden in Downtown ~ 5 Min to Beaches

Our bright and contemporary Heart Villa offers the quintessential Sarasota downtown and beach experience. It is nestled among tropical trees in a charming cul-de-sac in historic Laurel Park – right in the heart of downtown with loads of restaurants, boutiques, and sights on offer. Several fantastic beaches are just 5-mins ride away! And the villa's private garden is the perfect place to enjoy alfresco dining! We’ve poured our hearts & souls into this villa, it's our family business.

Guest favourite

Home in Sarasota

4.88 out of 5 average rating, 8 reviews

Slowtide Cottage on Siesta Key

A high-end luxury cottage retreat on Siesta Key. No parties here -- the space was designed and outfitted for those who want a quiet place to relax. 2 bed 2 bath Cottage situated on the Intracoastal water of Siesta Key adjacent to the community pool, tiki bar, fishing dock, fishing pier and deeded private beach access. Meticulously remodeled former ww2 USAAF Barracks from the old SRQ Air Force Base. All new electrical, plumbing, lighting (Buster & Punch), Arhaus furniture.

Superhost

Home in Sarasota

4.86 out of 5 average rating, 7 reviews

Warm, Luxury Oasis in Central Sarasota

Choose to stay at a home which has it all. Professionally designed and hosted by a 10-year SuperHost, this property offers incredible value. Superbly comfortable beds and linens, SUPER FAST internet, thoughtful furnishings, tons of activities & games, fully equipped for babies and toddler needs, extremely central location, large, high-end TVs, a jacuzzi, 2-person hammock, in-ground fire pit…. And fur babies welcome… you name it, this home has it. Welcome to Sarasota Paradise.

Guest favourite

Home in Sarasota

4.98 out of 5 average rating, 372 reviews

The Cottage at Central Park II

If you are looking for the perfect family home to cater to your every need, then look no further! With plenty of space to spread out, natural light that pours into every room, an expansive and private fenced in yard, screened-in porch and outfitted kitchen- this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

Guest favourite

Flat in St. Pete Beach

4.8 out of 5 average rating, 294 reviews

Fiesta Siesta: Bright+ Cozy+ Unforgettable (4plex)

🌵Fiesta Siesta – Where Every Day Feels Like a Party!🌴 Feed me tacos and tell me I’m pretty—because life’s too short for anything less! Welcome to Fiesta Siesta, a fun, vibrant escape just steps from Upham Beach in sunny St. Pete Beach. One of four uniquely themed units in a gated complex, this playful retreat is decked out in a vibey cactus theme that’s all about fiesta and siesta—because, why choose? Book now and let the fiesta begin! 🎉🌮

Guest favourite

Flat in Dunedin

4.98 out of 5 average rating, 233 reviews

My Favorite Place 🍊downtown & city approved

LEGAL, CITY APPROVED 1 bedroom apartment w full kitchen, living , dining & separate bedroom located on the red brick streets of downtown Dunedin. Private entrance. BIKES Super clean Private driveway free parking Two great bikes Great for couples Tastefully decorated. Comfortable Queen bed. Luxurious bedding. Super clean. Shampoo, conditioner, body wash, coffee, tea, drinking water provided. SUPER CLEAN No pets

Guest favourite

Apartment in Sarasota

5 out of 5 average rating, 11 reviews

100' from the beach, Spacious 2BR Beachside Oasis

Discover the allure of Siesta Key from the comfort of this 1200 sqft vacation rental, perched on the 2nd floor of the Point of Rocks Trip-Plex the peaceful Point of Rocks neighborhood. This two-bedroom, two-bath unit is an ideal retreat for families or groups seeking a blend of luxury, comfort, and accessibility to the beach.

Superhost

Cottage in Indian Rocks Beach

4.68 out of 5 average rating, 199 reviews

Beachy Paradise

FULLY REMODELED INTERIOR AND EXTERIOR 10/2023!! Your perfect getaway cottage! Only 100 steps away from one of the best beaches around. Shops and restaurants all within walking distance. Tennis and basketball courts are across the street for some good exercise! BTR #1955

Guest favourite

Cottage in Indian Rocks Beach

5 out of 5 average rating, 37 reviews

Upper Deck prime area no condos/crowds

The location is one of the best on the West Coast. I’ve had only 5 stars from my guests. Our places are fully stocked and very clean. This whole property is award winning! Plus, we attract artists -Also our cottages have appeared on many calendars, cards and artists' canvas.