Condo vacation rentals in Anna Maria

A stylish living room is presented, featuring a comfortable gray sofa paired with a decorative round coffee table. Brightly colored wallpaper adorned with shell patterns enhances the space, while large windows allow natural light to filter in, complemented by light-colored flooring.

4.93 out of 5 average rating, 136 reviews

Minutes to AMI • Walk to Beach & Bay

Experience the ultimate beachside retreat in this newly renovated 1/1 condo, located within walking distance to the serene beauty of Palma Sola Causeway Parks Bayfront beach, jet-ski rentals, and horseback riding and also a quick drive/bike from the beaches of Anna Maria Island. This well-positioned condo offers the perfect balance of convenience and tranquility, providing easy access to the natural wonders of the island and the vibrant attractions nearby, including canal fishing, jet skis, etc.

Adirondack chairs in soft blue are positioned on the sandy beach, offering scenic views of the ocean and coastline. The sun reflects off the water, enhancing the tranquil atmosphere, while a distant figure strolls along the shore. Lush greenery borders the sandy area.

4.94 out of 5 average rating, 167 reviews

Beach Escape & Pool, steps to Beach & restaurants

One block from beautiful beach & waterfront dining. Newly renovated Villa in quaint quiet condo building close to everything on Anna Maria Island. Pickleball across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. *Min. renter age 25. Two minute walk to beach, trendy Bridge Street shops, marina, restaurants, bars, boat tours, mini golf and more. Brand new beds, furniture & appliances. Kitchen has everything you need. Beach supplies in hall closet.

4.96 out of 5 average rating, 103 reviews

Steps to the beach! Condo with pool at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

4.98 out of 5 average rating, 226 reviews

A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.

Condo in Longboat Key

Sun-Kissed Memories: Open Thursday, March 26th!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

A heated pool is surrounded by a paved patio and lush tropical landscaping. Comfortable seating under an umbrella is positioned nearby, creating a relaxing outdoor space. The building above features a balcony, adding a vertical dimension to the inviting environment.

4.87 out of 5 average rating, 131 reviews

Steps from the beach

Perfect place to put your feet up and relax! One of four units in the condo gives your getaway a private feeling where you don't share the heated pool with many others, on a dead end road. The only unit overlooking the pool from the master bedroom. You'll be just one block from the beach making it tempting to go multiple times a day! The clean, modern decor makes it a great place for both short and long term visitors. Just a nature trail away from a grocery store, shops and restaurants.

A two-story yellow condo is highlighted against a clear blue sky. Palm trees line the pathway leading to a fenced pool area. The entrance features a covered balcony with white railings, offering a welcoming view of the surrounding tropical landscape.

4.9 out of 5 average rating, 104 reviews

Beachy Chic! 1st Floor Condo-Pool-Close to Beach

Enjoy this NEWLY RENOVATED FIRST FLOOR 2-bedroom 1 bath condo just a short easy 2-minute walk to the BEACH. The New Key West vibe includes a Custom White Kitchen w/ SS appl, Shiplap, luxury plank flooring, & W/D combo. The pretty modern bath was updated with custom quartz top vanity. Relax at the pool directly next door & enjoy morning coffee on the little covered patio. The 2nd bedroom can be made up as 2 twins or a King. Walk to wonderful restaurants & shops. Gas Golf Carts permitted.

5 out of 5 average rating, 165 reviews

Two beach chairs are placed under a large white umbrella on the pristine white sand. The tranquil blue water of the ocean is visible in the background, complemented by clear skies and palm fronds gently swaying in the breeze.

Condo in St. Pete Beach

Beachfront in Pass-A-Grille w/ 2 bikes

Enjoy an intimate and relaxing stay on the best stretch of the St. Pete Beach of Pass-a-Grille. Walk out your door to the white sand towards the famous Don Cesar or dine on your deck facing the water. Free parking, 2 bikes, SUP board, towels, umbrella, beach chairs, & cooler! We are allowed 3 rentals under 28 yearly. Please inquire to see if you are one of the lucky guests to come. We love long term guests but understand not everyone can do this and simply need a little escape! 🤍

A spacious living area features a light-colored sofa against a vibrant tropical leaf mural. A sleek white entertainment unit holds a flat-screen TV, complemented by a decorative lamp and a colorful area rug underfoot. Natural light filters through window blinds.

4.98 out of 5 average rating, 162 reviews

KING Bed + AMI Beaches + Beach Gear!

🎙️🦩Welcome to the Retro Flamingo! Your tropical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this retro “Old Florida” themed condo!

A heated pool is surrounded by lush greenery and palm trees. Lounge chairs are positioned along the perimeter, and a gentle blue hue reflects off the water. The two-story buildings in the background create a tranquil resort-like setting.

4.97 out of 5 average rating, 133 reviews

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean & comfortable. Sandy Pointe II is in a secluded setting, an easy walk to a less crowded, quieter section of beautiful AMI beach. Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! *NOTE- This unit is a walk-up, no elevator. 33 steps, spaced with 3 landings VRC # 20-000-272 Minimum stay 7 nights, Adult occupancy/4 , parking 2 vehicles & Quiet hours, 10 PM untill 7 AM

Superhost

4.87 out of 5 average rating, 23 reviews

Beachfront Newly Remodeled 2/1 -Right on the beach

TWO SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Open plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location right on the beach Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

The outdoor area features a heated pool with a rock waterfall, surrounded by lounge chairs. A thatched Tiki hut provides shaded seating, set within tropical landscaping. The villa's light blue exterior and white furnishings enhance the inviting atmosphere of the space.

4.93 out of 5 average rating, 153 reviews

Blanco and Sunset Villas on Anna Maria Island

Back Open Jan '25! Located just 200 steps from the beach you’ll have your feet in the sand in no time. A comfortable living area + fully equipped kitchen. Furnished with island décor and local art. Everything you need including a heated pool, large patio with a Tiki hut, tropical gardens, plus a private outdoor area with a shower for your comfort. Walk to everything – grocery, pharmacy, ice cream, breakfast, pizza, donuts, and the beach which is less than 2 minutes away.

A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.

4.97 out of 5 average rating, 198 reviews

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

Popular amenities for Anna Maria condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

Superhost

4.88 out of 5 average rating, 43 reviews

Tradewinds Deluxe North Cottage

4.95 out of 5 average rating, 41 reviews

Foxtail Palm: *Luxe Pool Oasis *Steps from Beach

A large, inviting swimming pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned on the stone patio, while a shaded umbrella provides relief from the sun. A stone feature adds a natural touch, completing the serene outdoor setting.

4.97 out of 5 average rating, 31 reviews

Sunset Villa D by Beach Boutique Rentals

Condo in Independence Square

An aerial view captures a spacious beachfront condo, surrounded by tropical greenery and sandy beach. Waves gently lap at the shore in the distance, while the nearby neighborhood features homes with varying architectural styles. The inviting atmosphere of Indian Rocks Beach is evident from this vantage point.

5 out of 5 average rating, 33 reviews

Beachfront Dream Condo

Aerial view of a coastal community featuring multiple multi-story buildings surrounded by lush palm trees. A tranquil pool area is visible, alongside a winding pathway leading toward the waterfront. The backdrop showcases the shimmering waters of Anna Maria Sound, enhancing the peaceful setting.

5 out of 5 average rating, 8 reviews

3BD Luxury-Incredible Views of Sunsets, Marina

An aerial view captures the serene shoreline of Anna Maria Island, with soft waves gently lapping at the sandy beach. Colorful beachside homes and lush greenery line the foreground, while the vast expanse of turquoise water meets the cloudy sky in the distance.

4.98 out of 5 average rating, 60 reviews

Hello Sunshine! BeachView Condo on Anna Maria Isl.

5 out of 5 average rating, 15 reviews

An aerial view captures the serene coastline of Anna Maria Island, with soft white sands meeting clear turquoise waters. The rental property is highlighted, surrounded by lush greenery and residential areas, providing a glimpse of the peaceful beachside community and nearby amenities.

Condo in Anna Maria

Barefoot Mermaid 1, steps to the beach

4.92 out of 5 average rating, 87 reviews

Condo in Tierra Verde

Your Island Escape! • Discounted Summer Rates

Pet-friendly condo rentals

5 out of 5 average rating, 17 reviews

A spacious pool area is framed by lounge chairs in vibrant turquoise. The inviting pool reflects the sky, with sun umbrellas providing shade. A wooden deck with steps leads to the upper unit of the duplex. Lush greenery surrounds the outdoor space.

Condo in Cortez

Tropical Haven *A

4.89 out of 5 average rating, 108 reviews

The exterior of a pink three-story condo is visible, surrounded by palm trees and tropical plants. A pool area features several lounge chairs and a circular table, with a covered balcony on the second floor. Light clouds decorate the sky, creating a relaxed atmosphere.

Condo in Sarasota

5213B Menorca Street - Siesta Key Village Condo

4.94 out of 5 average rating, 106 reviews

A spacious open-concept living area includes a sleek kitchen with modern appliances and ample counter space. A dining table with six chairs and a pool table provide options for entertainment. Bright overhead lights create a welcoming atmosphere, with light-colored cabinets complementing the room.

Condo in Madeira Beach

Penthouse,intercoastal, 3/3 views/heated pool

4.9 out of 5 average rating, 182 reviews

An outdoor seating area is shown with a glass-top table surrounded by four blue chairs. Two charcoal grills are positioned nearby under palm trees, with a view of the water in the background. The screened cabana features a thatched roof, providing a relaxing atmosphere.

Condo in Treasure Island

Waterside Studio in the heart of TI, walk to beach

Condo in Gulf Gate Estates

The studio features a modern kitchen with white cabinetry and a large countertop. A flat-screen TV is mounted on the wall, and natural light enters through sliding glass doors that lead to the private garden. A compact dining table and a plush blue ottoman add functionality.

4.97 out of 5 average rating, 125 reviews

Modern Studio · 5 min from Siesta Beach

4.95 out of 5 average rating, 116 reviews

Condo in St. Petersburg

Updated Condo-Heated Pool-Private Balcony

Condo in Indian Beach-Sapphire Shores

5 out of 5 average rating, 8 reviews

Luxury retreat Condo The Strand Water View w/ Den

Condo in Clearwater Beach

Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.

4.95 out of 5 average rating, 317 reviews

Steps 2 beach! Beachy and Luxurious! Easy Living!

Condo rentals with a pool

4.96 out of 5 average rating, 48 reviews

A clear, inviting pool is surrounded by a landscaped area with tropical plants and palm trees. The bright orange exterior of the building contrasts with the lush greenery. Chaise lounge chairs are positioned nearby for relaxation.

Condo in Siesta Key

Siesta Key Village, Pool, Beach Access 4-min Walk

Condo in Redington Shores

A bright living area features large windows offering sweeping ocean views. A sleek white sectional sofa sits atop a soft area rug, accompanied by a stylish coffee table set with glasses and a bottle. A flat-screen television is mounted above an electric fireplace, adding comfort to the space.

4.98 out of 5 average rating, 62 reviews

Fall dates avail! Beachfront 2/2 w/Jacuzzi & FP

An aerial view showcases a resort-like community surrounded by lush palm trees. A curvy swimming pool is centrally located, with bright lounge chairs neatly arranged around it. A charming patio area features seating, providing a setting for relaxation amidst the landscaped greenery.

5 out of 5 average rating, 34 reviews

Coastal Oasis Condo w/ Luxury Resort Amenities

5 out of 5 average rating, 45 reviews

Freshly Renovated Vacation Villa at Shorewalk

4.93 out of 5 average rating, 60 reviews

A private balcony overlooks the beach and Gulf of Mexico. Two red chairs are positioned for comfortable seating, while a railing provides safety and unobstructed views. The serene landscape features green grass leading to the sandy shore and the calm blue waters of the ocean.

Condo in Treasure Island

INCREDIBLE SUNSET BEACH OCEANFRONT TOP FLOOR CONDO

The exterior of a multi-story building is depicted, featuring vibrant orange walls and teal shutters. Palm trees line the entrance, and a spacious driveway made of pavers leads to the garage below. The design incorporates balcony spaces and decorative architectural elements.

4.91 out of 5 average rating, 58 reviews

Gorgeous Gulf Views - Beachfront 2BR/2B Condo

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

4.97 out of 5 average rating, 126 reviews

A&A's Paradise near IMG & Anna Maria beaches

A spacious living area features comfortable blue sofas adorned with decorative cushions. A wooden coffee table occupies the center of the room, surrounded by a light area rug. Natural light streams through large windows, enhancing the airy atmosphere, while a ceiling fan adds to the comfort.