Condo holiday rentals in Downtown Sarasota

A bright and airy living space features a modern sofa facing a sleek coffee table. The open kitchen is visible in the background, showcasing white cabinetry and bar seating with stylish stools. Light fills the room through large windows, enhancing the spacious feel.

4.96 out of 5 average rating, 128 reviews

Your Modern Beachside Getaway!

Search no more… we have it all! Enjoy this spectacular, newly remodeled beachside home in Siesta Key, equipped with a modern kitchen, hotel luxury pillow-top bed, and high-end finishes throughout! Amenities include private beach access (beachside 3 minute walk), pool access, patio, courtyard, BBQ, parking, and more. And the cherry on top, you’re right across the street for a plethora of restaurants, shops, and conveniences giving you everything you need to enjoy the best of Siesta Key!

A modern living room features a light-colored leather sofa and armchairs, complemented by a colorful area rug. A wall-mounted TV is positioned against a textured stone wall, with natural light filtering through sliding glass doors that lead to a screened-in patio.

5 out of 5 average rating, 135 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to beautiful Siesta Key, the #1 beach in the country! Gorgeous newly renovated one bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach gear • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

4.94 out of 5 average rating, 144 reviews

A charming studio space features a queen size bed with a white blanket and decorative pillows. A small nightstand sits beside the bed, and a light is positioned for reading. Natural light enters through a large window with blinds, complementing the wood-look flooring.

Condo in Lido Key

Lido-Key- Tiny Studio Holiday Cottage-A

We are Open after Hurricane Helene! **No Kids allowed** Lido Key- 7-10 min walk to the beach & St Armands. Quaint main floor tiny (smaller than a hotel room) studio is in a Great location and an affordable way to enjoy this popular area. This cozy cottage features a Queen size bed, refrigerator, stove, microwave, coffee maker, washer & dryer, and fully stocked cooking items & dishes, Beach chairs, umbrella & towels are provided. Located at 170 Roosevelt Dr Drive, Sarasota, Fl 34236.

Aerial view showcasing a sandy beach surrounded by vibrant turquoise waters. Lush greenery is visible along the shoreline, with boats floating in the clear water. The scene captures a serene coastline, inviting guests to explore the natural beauty.

4.93 out of 5 average rating, 207 reviews

Steps away from beach and village! #1 in Siesta!

The Little Sandy... Your secret hideaway Incredibly located Two bedrooms, one bath Sleeps 6 easily Bring the kids...or not Walk everywhere. 3-minutes to the beach, 8 to Siesta Village Super-fast Wi-fi! Icy A/C Lovely pool Play in the water, play on the sand, play in the village Rinse and repeat Comfy beds, soft towels A great night's sleep And the best hosts on Airbnb Tradewinds included free of charge. So book now and find your Siesta-self Just like you, only funner.

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, 152 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!

4.98 out of 5 average rating, 218 reviews

Condo in Longboat Key

Oceanfront: Lots of January Availability!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located 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 onward to the secluded beach with loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort!

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

4.97 out of 5 average rating, 350 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

A well-appointed kitchen features light-colored cabinetry and countertops, with modern appliances including a microwave and oven. An island provides additional workspace, while a dining area is visible in the background. Soft lighting creates a welcoming ambiance throughout the space.

4.96 out of 5 average rating, 114 reviews

Palm Bay Club! Resort Style Living on Siesta Key!

Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

A serene community pool is surrounded by a fence and complemented by lounge chairs positioned nearby. The pool's clear blue water reflects the sunlight, while the yellow exterior of the building provides a warm backdrop. Windows with awnings complete the inviting atmosphere of the area.

4.94 out of 5 average rating, 158 reviews

January Discount: $165/night!

2 BDRM/2 BTHRM condo very close to Siesta Key (3 min. drive or 20 min. walk). Totally UPDATED! Quality furnishings, super clean, ideal location. Have it all: Spacious condo in a peaceful setting. Just a few minutes drive over the south bridge to Siesta Key. Walking distance to great restaurants and shops on and off the key. Everything is within easy access by walking, car, bike, or free beach shuttle service. Come enjoy everything Sarasota has to offer.

4.89 out of 5 average rating, 122 reviews

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

4.92 out of 5 average rating, 150 reviews

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

A fire table is positioned in view of a vibrant sunset, reflecting shades of orange, pink, and purple across the sky. The scene is framed by large glass panels, offering unobstructed views of the horizon, enhancing the outdoor experience.

4.91 out of 5 average rating, 138 reviews

New Luxury 3/3 Condo in Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features wonderful unobstructed water views of Anna Maria Sound and Tampa Bay. 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 Downtown Sarasota condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.92 out of 5 average rating, 71 reviews

The image captures a shared pool area surrounded by lush greenery and palm trees. Lounge chairs with blue umbrellas are positioned around the pool, which is enclosed with a white fence. A pathway leads through well-maintained landscaping, enhancing the inviting outdoor space.

Condo in Saint Armands

Steps from Lido Beach & St. Armands Circle

A cozy deck area features outdoor seating with two bar stools and a small table adorned with flowers. Palm trees provide shade while a serene waterfront view is visible, with a private dock and a pool in the background.

4.98 out of 5 average rating, 51 reviews

Bayside Escape-Condo w/ Dock, Pool, and Near Beach

The heated pool is bordered by a stone patio and surrounded by lush greenery. Umbrellas and lounge chairs provide seating options. A tiki bar is visible in the background, with a scenic view of the water and distant trees, creating a relaxing outdoor space.

4.96 out of 5 average rating, 23 reviews

Just renovated 2bed/2bath Siesta Key Beach Condo

A bright and inviting living area features a light gray sofa adorned with colorful pillows. A teal coffee table sits atop a striped rug, complementing the vibrant decor. Large glass doors provide a view of the lake, with outdoor seating visible on a patio.

4.98 out of 5 average rating, 62 reviews

The Starfish Cottage

A pelican is perched on a wooden railing overlooking the ocean, with its long beak prominently displayed. The water reflects gentle waves beneath a cloudy sky, while a sign stating 'No Sitting or Standing on Rails' is positioned below the bird.

4.66 out of 5 average rating, 110 reviews

Hotel Style w/pool & Tiki Grill

A sign marking Siesta Beach as the '#1 Beach in the USA' is prominently displayed at the entrance. A sandy pathway leads to the beach, flanked by green vegetation and palm trees. Beachgoers and colorful umbrellas can be seen in the background, emphasizing the lively atmosphere.

4.89 out of 5 average rating, 70 reviews

A Hidden Gem in Paradise

A spacious sleeping area displays two queen-size beds arranged with crisp white linens. A simple, modern decor is accentuated by a soft area rug. A vanity with a mirror and lamps can be seen in the background, complemented by a rustic sign that reads 'RELAX.'

4.84 out of 5 average rating, 43 reviews

Clean, cozy and very comfortable

Condo in Southside Village

The open-concept living and dining area showcases a modern design with a dining table set for six and stylish seating arrangements. Light grey curtains frame large windows, while a textured area rug adds comfort. Artwork adorns the walls, contributing to the space's elegant atmosphere.

5 out of 5 average rating, 13 reviews

Sarasota Southside Village 2 BR Luxury Apartment

Pet-friendly condo rentals

4.96 out of 5 average rating, 24 reviews

The exterior of the condo showcases a modern design with a covered porch featuring a seating area. Palm trees and landscaped greenery are present, contributing to a relaxed atmosphere. The structure features large windows, allowing natural light to illuminate the white façade.

Condo in Nokomis

Walk to the beach from this lovely 2 bedroom condo

4.87 out of 5 average rating, 55 reviews

A light-filled living area is furnished with a curved sectional sofa adorned with colorful cushions. A round coffee table rests on a floral-patterned rug, surrounded by decorative plants and coastal-themed artwork. Large sliding doors lead to an outdoor space, framed by sheer curtains.

Condo in Cove

J&J Island Time

A sandy beach scene is presented, featuring a sign reading 'Siesta #1 Beach in the USA.' A palm tree stands nearby, offering shade, while a wooden bench invites visitors to sit and enjoy the view. The calm ocean is visible in the background under a clear blue sky.

4.98 out of 5 average rating, 54 reviews

Siesta Key w heated pool arcade & pet friendly

A modern living area features a comfortable sectional sofa, accented by textured cushions. A flat-screen TV is mounted on the wall above a wood panel, while large sliding doors invite natural light and provide access to the patio. Indoor plants add a touch of greenery.

4.85 out of 5 average rating, 123 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

4.9 out of 5 average rating, 50 reviews

Updated condo minutes to Siesta Key Beach

The image features a community swimming pool bordered by a deck with lounge chairs. Bright yellow buildings with arched windows and red awnings provide a vibrant backdrop. Lush greenery, palm trees, and blue skies enhance the inviting atmosphere of the pool area.

4.85 out of 5 average rating, 52 reviews

2bed/2bath Condo next to Siesta Key ~A Hidden Gem

4.96 out of 5 average rating, 101 reviews

Condo in Holmes Beach

Steps to the beach! Updated Condo at The Terrace

4.99 out of 5 average rating, 145 reviews

A modern kitchen area features pale blue walls and a round dining table set for four. Stainless steel appliances, including a microwave and oven, are visible. A decorative light fixture made of translucent discs hangs above the table, adding a coastal touch to the space.

Condo in Holmes Beach

Short Stroll to the Surf! ~ Make Memories on AMI

Condo rentals with a pool

5 out of 5 average rating, 20 reviews

Condo in Longboat Key

Sunset and Beach view unit 402

5 out of 5 average rating, 15 reviews

An updated kitchen features sleek white cabinetry and modern stainless steel appliances. A spacious island provides additional counter space. Stylish lighting fixtures hang from the ceiling, while a decorative mirror and lamp enhance the room's design. Subtle textures and finishes add to the contemporary feel.

Condo in Venice

Location! Gulf Condo @ S. Jetty 30 day minimum

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, 121 reviews

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

5 out of 5 average rating, 15 reviews

Your Beachside King Suite Retreat!

A dining area is presented with a large wooden table surrounded by blue upholstered chairs. Sunlight pours through expansive windows, revealing views of the turquoise waters and sandy beach beyond. A beach-inspired artwork decorates the wall, adding a touch of coastal charm.

5 out of 5 average rating, 68 reviews

Breathtaking Beachfront Views in Siesta Key

5 out of 5 average rating, 98 reviews

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

4.95 out of 5 average rating, 60 reviews

Top Floor Beautiful View Condo-Shore To Please

The master bedroom features a spacious bed, complemented by bedside lamps. A seating bench is positioned at the foot of the bed. A ceiling fan provides airflow, while light neutral tones enhance the serenity of the room. An en-suite bathroom is visible through an open doorway.