Condo vacation rentals in 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, 169 reviews

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

Welcome to Mi Casa Siesta on 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

A heated pool is surrounded by a tiled deck, with lounge chairs available for guests. Palm trees and blue umbrellas create a tropical atmosphere, while the beach and ocean are visible beyond the pool area under a clear blue sky.

4.94 out of 5 average rating, 155 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Amazing 2nd floor unit in building C at the Sarasota Surf & Racquet Club. This fully furnished 2 bed/ 2 bath condo offers a resort view and just steps away from the white sands of Siesta Key Beach. This unit is recently updated with an open floor plan, featuring stainless steel appliances, granite counter tops, kitchen bar with stools, living room, and dining room. This unit has flat screen tv's, ceiling fans, and maid service including linens and bath towels. Washer/dryer located down the hall

A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.

4.95 out of 5 average rating, 146 reviews

NO Stairs, Siesta beachfront. Walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

4.79 out of 5 average rating, 108 reviews

Beachwalk Townhouse with view of Gulf of Mexico

Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.

4.85 out of 5 average rating, 109 reviews

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

4.98 out of 5 average rating, 251 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

Island Time: Discounted August & September!

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...!

4.86 out of 5 average rating, 137 reviews

Beach Retreat - Jamaica Royale Unit #52

Casually elegant condo fully remodeled in 2025, and very close to beach! One bedroom, one bath unit includes quartz kitchen counters, new appliances, king bed and relaxing patio. Perfect size for 2 guests! No need to cross busy roads to get to stunning white sand; just a 5 -10 minute walk along lush grounds which boast 3 heated pools. Beach gear provided, and unit is stocked with linens and kitchen utensils. Minutes away from Siesta Village and other wonderful dining and activities.

A beachfront pool area is shown under a bright sky, featuring palm trees and umbrellas around the pool. Guests are seen enjoying the water, with lounge chairs and colorful towels placed around the poolside. The ocean is visible in the background, completing the serene atmosphere.

4.86 out of 5 average rating, 153 reviews

Private Beach Siesta Key Resort Jamaica Royale

Jamaica Royale is a Beach Front Oasis, offering a private community with our own beach access and 3 heated pools . Enjoy our sidewalks, directly to the beach with no roads to cross; only residents are allowed onto the property, offering a family-safe paradise! Put your toes in the white sands of Siesta Key, where we have a private beach pavilion and lounge chairs! Look at our overview, to see our excellent location! We are in the first set of villas, closest to the beach.

A tranquil pool area is surrounded by palm trees, reflecting the clear blue sky. Lounge chairs are positioned around the pool's edge, inviting relaxation. The sun casts a warm glow over the scene, enhancing the peaceful ambiance of the resort.

4.98 out of 5 average rating, 137 reviews

Siesta Key For Me @ The Palm Bay Club

🏖️ Newly Renovated Siesta Key Condo | Ocean + Bay Views | Sleeps 6 📍 Bayside Suite at The Palm Bay Club | Walk to Beach ✨ ALL-NEW RENOVATIONS MAY 2025! Brand new bathrooms, flooring, doors, trim, granite countertops & more—be among the first to enjoy our stylish upgrade! Welcome to Condo #310 at The Palm Bay Club—a 2BR/2BA bright and breezy bayside condo with water views, modern upgrades, and private beach access just a short walk away. Sleeps up to 6 guests comfortably.

A serene pool area is bordered by palm trees, reflecting the gentle hues of a sunset. Lounge chairs are arranged around the pool, and a shaded cabana is visible in the background. The tranquil water mirrors the evening sky, enhancing a peaceful atmosphere.

4.97 out of 5 average rating, 133 reviews

Private Beach with Loungers · 2 Pools & Bay View

Beachside resort life for families, groups and remote workers seeking easy beach access and active days. This oversized & Fully Renovated 2‑bed, 2‑bath condo sits in a gulf-to-bay complex so you can walk to the famed Siesta Key sand and hop the island trolley outside your door. Enjoy bay views, unwind in heated pools and the hot tub, use the on-site gym and courts, and take advantage of provided beach chairs, umbrella and wagon for effortless beach days.

4.92 out of 5 average rating, 165 reviews

Condo in Sarasota

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!

4.87 out of 5 average rating, 209 reviews

An aerial view shows a two-story beachfront property with direct access to the beach. A shared pool is visible in the center, surrounded by lounge chairs. The studio unit is indicated with a blue circle on the left, featuring a patio area and proximity to the sandy beach.

Condo in Longboat Key

The Beach Condo #107 Beachfront Full View

Unit #107 has private beach access. Only a few steps to the beach will full gulf view. This end condo unit is quiet, ground floor . It is a small studio: new queen murphy bed and queen sofa bed. No separate bedroom. Limited initial limited supply of products/soaps/towels. Common use W/D across from unit. This is a small studio at 330 sq ft. It has been recently remodeled. Grounds, unit, pool recently renovated due to hurricanes.

Popular amenities for Siesta Key condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Condo rentals with a pool

An aerial view captures the expansive white sand beach and turquoise waters, lined with beachgoers. The surrounding buildings and amenities are visible, including pools and recreational areas, creating a vibrant coastal atmosphere. Cloud patterns add depth to the bright blue sky above.

4.94 out of 5 average rating, 137 reviews

Beautiful White Sand Siesta Key Beach

4.93 out of 5 average rating, 161 reviews

Gulf Views | Walkable | Spacious

Superhost

A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.

4.88 out of 5 average rating, 146 reviews

Crystal House on Siesta Key Beach

A view from above showcases the lush, landscaped grounds of the condo complex, featuring curving pathways and palm trees. In the foreground, a heated pool is visible, with beach access just beyond. The serene beach and expansive ocean create a welcoming atmosphere.

4.83 out of 5 average rating, 149 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

A modern living area showcases a comfortable sectional sofa and armchair, complemented by a wooden coffee table. A large flat-screen TV is positioned on a media console. Natural light floods the space through sliding glass doors that lead to a balcony, enhancing the open feel.

4.88 out of 5 average rating, 173 reviews

Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything

A bright living area features a white sectional sofa facing a modern fireplace set in a textured stone wall. A wooden coffee table sits atop a striped rug, with a beach-themed painting and a ceiling fan visible above, contributing to a relaxed ambiance.

4.89 out of 5 average rating, 127 reviews

Perfect Location in Siesta Key

4.96 out of 5 average rating, 110 reviews

Condo in Holmes Beach

Steps to the beach! Condo with pool at The Terrace

A brightly colored three-story building stands under a starry night sky, surrounded by palm trees. Exterior lights illuminate the vibrant walls and large windows. A paved driveway leads up to the garage, flanked by landscaped greenery.

4.88 out of 5 average rating, 126 reviews

5209B Menorca Street - Siesta Key Village Condo

Pet-friendly condo rentals

Condo in Gulf Gate Estates

A spacious studio features a cozy sleeping area with a queen bed dressed in soft linens, complemented by decorative pillows. Floor-to-ceiling windows provide natural light and a glimpse of the private garden. Soft earth tones create a calming atmosphere, and a textured rug adds warmth.

4.95 out of 5 average rating, 134 reviews

Hidden Gem Studio · Near Siesta Beach (5 min)

A clear view of the ocean is presented, complemented by lush greenery in the foreground. Buildings line the coastline, and a blue sky with light clouds enhances the scene, creating an atmosphere of tranquility and connection to nature.

4.97 out of 5 average rating, 33 reviews

Penthouse Beautiful Ocean Views

4.96 out of 5 average rating, 117 reviews

A sandy pathway leads to the beach, framed by lush greenery and tall grasses. The gentle waves of the ocean are visible in the distance, with a clear blue sky overhead. Sunlight casts a warm glow on the pathway, inviting relaxation.

Condo in Venice

Short walk to beach 4, King bed, Dog Friendly

5 out of 5 average rating, 7 reviews

Condo in Bradenton Beach

Bayfront • Rehabbed • Pickleball • Private Beach

An aerial view reveals the vibrant community surrounding this vacation rental, with colorful buildings and lush palm trees. The coastline stretches in the distance, showcasing the beach's sandy shoreline and turquoise waters, while the local neighborhood features a mix of residential and commercial structures.

4.98 out of 5 average rating, 64 reviews

100 Steps to beach access & 5-min Village walk

4.97 out of 5 average rating, 208 reviews

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.

Condo in Bradenton

Luxury 3/3 Margaritaville Resort

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, 153 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

Condo in Gulf Gate Estates

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

4.89 out of 5 average rating, 193 reviews

Lake View 1BR Condo | Heated Pool Near Siesta

Weekly condo rentals

The image captures a vibrant sunset over the horizon, casting warm hues across the sky. Palm trees line the foreground, creating a tropical ambiance. The view also includes a peaceful road and glimpses of the beach beyond, emphasizing the proximity to coastal scenery.

4.97 out of 5 average rating, 60 reviews

Siesta Key Beach front 2 bedroom condo w/ parking

Aerial view captures the pristine beach alongside the expansive manicured grounds of a gated community. The layout features several buildings with red roofs, centered around a heated salt water pool. The shoreline and beach-goers are visible in the distance.

4.98 out of 5 average rating, 63 reviews

Siesta Dunes 1st Floor Beach Front Retreat

Superhost

A spacious living area is featured with large windows that allow natural light to fill the room. Comfortable seating includes a sectional sofa, two chairs, and a round coffee table. An expansive flat-screen TV is positioned on the floor, providing entertainment options.

Condo in Sarasota

5 out of 5 average rating, 4 reviews

North Water View - Residence 310

Superhost

A spacious balcony is showcased, featuring a dining table with six chairs. The area is surrounded by a white railing, with views of palm trees and a vibrant sky during twilight. Large sliding glass doors lead into the interior, creating a seamless connection.

4.79 out of 5 average rating, 63 reviews

Beach Front Haven

4.99 out of 5 average rating, 178 reviews

A spacious living area features a blue sofa and striped armchair, complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, showcasing views of the turquoise Gulf. Light-colored cabinetry and decorative shelving enhance the inviting atmosphere.

Condo in Bradenton Beach

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

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, 97 reviews

Breathtaking Beachfront Views in Siesta Key

An expansive view showcases the Gulf waters and sandy beach from a fourth-floor corner unit. Lounge chairs are visible on the beach, while a balcony railing frames the scene. Bright skies are complemented by gentle waves rolling onto the shore.

4.94 out of 5 average rating, 77 reviews

Beach & Pool Open! Direct Beachfront Condo! Sunset

A light-filled living room features a comfortable navy sofa with decorative cushions, a patterned armchair, and a round accent table. A coffee table rests on a woven rug, while built-in shelves display books. Soft lighting is provided by stylish pendant fixtures and table lamps.