
Villa rentals near Anna Maria Island
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Top-rated villa rentals near Anna Maria Island
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Heated Pool! Huge Walk In Shower! 5 min to beach!
Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

Starfish House - 2bed/2bad
An Anna Maria Island Vacation to remember is waiting for you at Starfish Beach #4. This charming complex is small and quiet, perfect for a relaxing beach getaway. A shared pool is available in the courtyard. You'll enjoy being just steps from the Anna Maria Public beach access. With a short walk, finding your place in the sand each morning will be easier than ever! 50 yards to the BEACH! Bed size: 1 K, 1 Q, sleeper Baby accessories available for rent. Snoo Bassinet high chair pack and play

Entire Standalone Villa,1.2k sf,1 block Lido Beach
Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and family. The Villa is located 1 block away from world famous Lido Beach, a 7 min walk to St Armand's Circle, and a short 3 mile drive to grocery shopping & the excitement of downtown Sarasota. The 2 bdr villa comfortably sleeps up to 6 people and features a private outdoor patio, spacious dining area, in-unit washer/dryer & dedicated parking. Come enjoy a taste of paradise!

Northshore BeachHouse West Anna Maria Island
Nine houses away from the white sandy beaches, Pine Ave and Northshore Drive is an adorable beach home located on Anna Maria Island. It is the perfect vacation beach house located at the north end of the historic village of Anna Maria Island. Just steps away from Pine Ave, the beach, restaurants, and shopping, guests can walk conveniently everywhere. Jeff and I have lived and worked here on Anna Maria Island for over 20 years, and would love to share our little piece of paradise with you!

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach
Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

Duplex - just mins to Siesta Beach - Pet Friendly
This is a 2/1 in Sarasota's Historic Laurel Park that offers a great downtown and beach experience! Walk/bike to historic downtown with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the lanai & fenced backyard for privacy . Grill & enjoy your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk & check out the historic homes in the area! Short term rental number VR24-00222

Luxury Villa with Pool, Game Room, Near Beach
Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. • Bedrooms: 4 private suites, plush linens to ensure restful nights. • Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. • Heated pool & sun loungers • Arcade-style game room • Fast Wi-Fi & 5-star cleanliness • Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today! VR24-00060

Gulf side. 1 house to beach. Peaceful 2 king beds
Construction upgrades complete! 30 second walk to gorgeous beach with amazing sunsets and miles of beachfront. Tucked away on a quiet street, a hidden gem away from busy condos. 1 of 3 units in a small villa on the beach side. Walk to restaurants. Beach towels, chairs & cooler. Washer/Dryer in unit, central AC, Wi-Fi, free parking in front. 2 bedrooms have King beds, 1 bedroom has 2 Twins (this room has W/D and extra sofa). Blackout curtains & comfy mattresses in all bedrooms.

The Tropical Oasis, w/ Solar Heated Pool and Games
Welcome to your private, tropical escape! Unwind by the solar-heated pool in a screened, mosquito-free lanai. FUN & GAMES: Enjoy Billiards (Pool Table) 🎱, Foosball, Cornhole, board games, and 3 Smart TVs 📺. PRIME LOCATION: Only 5 min 🚗 to Indian Rocks & Bellaire Beach, FL Botanical Garden, and dining. Essentials: 🌞 Heated Swimming Pool (Private!) 🎮 Billiard Table / Foosball Table / Cornhole / Boardgames and more! 🛏️ 4 Queen/Full Beds 🧺 Beach Amenities

Anna Maria Island Beach Getaway – Sleeps 6
Just a 8-minute walk from the sugar-white sands of Anna Maria Island and nearby shops and dining, this stylish home offers a resort-style stay with pickleball, tennis, and basketball courts, a park, and a boat ramp—all steps away. This 2-bedroom, 2-bath home, plus an air-conditioned Florida room, sleeps 6 with two queen beds and two twins that convert to a king. Relax in the private backyard or cook in the full kitchen for the ultimate island getaway.

Dolphin Cove Waterfront St. Pete Beach w/ Pool
THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

Boho -Minimalist villa
Welcome to our Boho Minimalist Villa 4311 unit B with a 2 bedroom and 1 bathroom. Conveniently located in the heart of Tampa, Florida. “Points of interest” to visit and enjoy while you are here: Raymond’s James Stadium, New York Yankees Training Camp, Hillsborough Community College, International Tampa Airport, Downtown Tampa, Midtown within less than 10-minutes’ drive enjoy a great afternoon eating at many local restaurants.
Popular amenities for villa rentals near Anna Maria Island
Private villa rentals

IRB Harbor House Semiprivate Waterfront Pool Villa

Luxury 4-Bedroom Pool Retreat Near Siesta Key

Newly Remodeled Luxury Beach Villa on Siesta Key!

Remodeled Mid-century POOL house

5 min to Siesta Key, Heated Pool, BBQ, Fast WiFi

Lakefront 2BR • Perfect for IMG & Long Stays

Coastal Villa w/ Amazing Courtyard - Splash Pad!

Siesta Key*PRIVATE BEACH*Gulf Side*Heated Pool
Luxury villa rentals

Newly Renovated- 150 Yards to Beach & Restaurants!

Private Beach Villa | Charming Decor | Sunset View

Luxury home in the heart of South Tampa & POOL!

Walk to Beach (4 min), Pool, Private Roof Deck

5 BR Luxury Beach Villa: Heated Pool & Games Room

Paradise with a pool, pier and private beach area

Waterfront Heated Pool, Sleeps 20 - 4plex

Luxury Villa w/ Private Pool
Villa rentals with a pool

Paradise Villa- Sarasota

Villa Perdomo Family

Relax just steps from beach & Gulf of America

Villa Siesta II -Dwntn Secret & pool near beaches!

Siesta Villa

The Citrus Hideout – SK Collection

Your own tropical paradise in Sarasota

River Pointe 3/2 Lakefront Home with Heated Pool
Villa rentals with a hot tub

[TRENDlNG] Modern 5BR Pool Villa + Arcade & Sauna

Bean Point Residence Unit B by SeaBreeze Vacation

La Villa, 1 of 4 rentals on-site. Heated Pool!

NEW! Waterfront Hot Tub, Heated Pool, & Golf Cart

Modern Luxury Villa - Heated Pool Spa, Game Room

Relaxation awaits in this bohemian inspired villa

Villa Blanca - Waterfront Midcentury Modern Home

Waterfront Condo w/ Kayaks, Resort Pool, Sarasota
Quick stats about villa rentals near Anna Maria Island

Total vacation rentals
Explore 40 vacation rentals in Anna Maria Island

Nightly prices starting at
Anna Maria Island vacation rentals start at G$27,196 GYD per night before taxes and fees

Verified guest reviews
Over 1,020 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Anna Maria Island vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Anna Maria Island rentals

4.7 Average rating
Anna Maria Island stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Rentals with a kayak Anna Maria Island
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- Rentals with a hot tub Anna Maria Island
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