Condo vacation rentals in Siesta Key

A modern bedroom features a spacious bed with crisp linens and a light-colored throw. A wooden dresser stands against the wall, and a framed artwork of a cow adds a touch of character. Subtle lighting from the bedside lamps enhances the inviting atmosphere.

4.87 out of 5 average rating, 309 reviews

[Beach Retreat] modern condo +5 min. walk to beach

5 min walk to beach and bikes onsite to rent.. Relax and recharge at this beautiful modern two bedroom Siesta Key condo. This is a fully remodeled second floor end unit with no unit above. The open layout provides excellent light throughout. Wonderful tile wood floors and a private screened in patio to sip your morning coffee. The warm sun and white sand beach awaits... beach gear (2chairs, towels, beach wagon)included complimentary -plus 2 beach cruisers to rent ($40 each per stay)

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.

4.9 out of 5 average rating, 134 reviews

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

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, 102 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.

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.

4.98 out of 5 average rating, 225 reviews

Sun-Kissed Memories!

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 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, 146 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

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, 363 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. If we are booked check out our additional units under our profile.

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, 125 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.

The kitchen features modern appliances including a stainless steel refrigerator, an oven, and a microwave. White cabinetry complements the granite countertops, while pendant lighting provides illumination. A breakfast bar with white stools offers an inviting space for casual dining.

4.91 out of 5 average rating, 114 reviews

Oceans2

This condo is set in the perfect location between the beach and the bay! Soak up the sun at the heated pool, enjoy the tiki hut, or try your luck on the fishing pier, all while viewing the boats on the intercoastal as they pass by. Included is a private deeded beach access that is an easy 5 min walk . Hop on the free trolley right outside your door to go to Siesta Key Village with plenty of restaurants, bars and shops only .5 miles away. Boat slip available for up to 24' .

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.

4.97 out of 5 average rating, 117 reviews

Palm Bay Club! Resort 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.

An aerial view of the Sea Shell condominium displays a four-story building with balconies facing the ocean. The bright blue sky and ocean can be seen beyond the structure, emphasizing the inviting coastal location.

4.92 out of 5 average rating, 148 reviews

Sea Shell Ocean View On Beach Walk Everywhere Pool

Enjoy ocean views in this 2 bed 2 bath spacious beach side 4th floor condo at Sea Shell Updated coastal decor across from Capt Curts, restaurants, grocery, coffee, ice cream Easy to WALK everywhere No car needed Perfect location Great for families Sleeps 6- 1 king & 2 queens & walk in closets Balcony with GULF views Private beach steps away from bldg. Free beach loungers. POOL Siesta Beach #1 in US Quick Wifi Superhost- 325+ reviews that ave FIVE STAR!

A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.

4.91 out of 5 average rating, 122 reviews

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

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.

4.88 out of 5 average rating, 115 reviews

Perfect Location in Siesta Key

Beautiful 1400 sq. ft townhome unit in the quiet, well-maintained and desirable Village West in Siesta Key. Relax and enjoy the finest crystal quartz sands just steps away. Only one minute walk to all shops, restaurants and main amenities in the famous Siesta Key Village.This 2 bedroom, 2 bathroom townhome offers split floor plan with cathedral ceiling. Everything included to have a seamless vacation.

Popular amenities for Siesta Key condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Condo rentals with a pool

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.

4.97 out of 5 average rating, 58 reviews

Siesta K- Kayak, Boat Dock, Pool, & walk to Beach

A refreshing cocktail is displayed on a wooden table, featuring vibrant garnishes of a cherry and a slice of lemon. The background showcases a serene beach scene, with soft white sand and calming turquoise waters under a clear blue sky.

4.9 out of 5 average rating, 115 reviews

#1 Beach- Super Clean- 2br/2bth Townhouse- 1400sf

4.98 out of 5 average rating, 99 reviews

The living area features a seating arrangement with two blue sofas and a light coffee table. A ceiling fan is present, along with a beige recliner. Large glass doors open to a lanai, allowing natural light to fill the room, complemented by coastal-themed art on the walls.

Condo in Holmes Beach

A Coastal Retreat Steps From the Sea

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, 52 reviews

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

A comfortable living area is furnished with two light-colored leather sofas and a circular glass coffee table displaying decorative items. Soft lighting is provided by a floor lamp, and framed art is mounted on the walls, adding a touch of decor. The space opens to a kitchen area in the background.

4.96 out of 5 average rating, 74 reviews

Charming Siesta Key Condo Just Minutes from Beach

5 out of 5 average rating, 3 reviews

2BR Beach Club – Beach, Heated Pool & Hot Tub

Condo in Indian Beach-Sapphire Shores

A circular pool is surrounded by modern white buildings, with palm trees dotting the perimeter. The clear blue water reflects the sky, and a poolside lounge chair is positioned near the edge. Paved stones create a pathway around the pool area.

5 out of 5 average rating, 38 reviews

Chill Sarasota Hideaway

Condo in Gulf Gate Estates

4.95 out of 5 average rating, 20 reviews

Lanai w/ Pool Views • Minutes to Siesta Key

Condo rentals with a hot tub

4.92 out of 5 average rating, 74 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

Condo in Indian Beach-Sapphire Shores

A spacious patio provides a serene view overlooking Whitaker Bayou, with boats moored along the water. A round dining table, surrounded by white chairs, offers an inviting spot for meals while enjoying the scenery. The area is complemented by a colorful artwork piece on the wall.

5 out of 5 average rating, 13 reviews

Modern 1/1.5 Waterfront at The Strand

4.8 out of 5 average rating, 64 reviews

Luxury Condo! Palm Bay Club Resort-Style Living

4.97 out of 5 average rating, 197 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

An aerial view captures the serene landscape of the Gulf Coast, showing the expanse of white sand beaches adjacent to the turquoise waters. The property is highlighted within a circle, showcasing nearby amenities, including a tennis court and peaceful bay areas. Lush greenery frames the scene.

5 out of 5 average rating, 6 reviews

Sun, Sand & Serenity at Longboat Key 2BR Condo

4.97 out of 5 average rating, 126 reviews

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.

Condo in Bradenton

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

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, 76 reviews

Breathtaking Beachfront Views in Siesta Key

A spacious sleeping area features a plush king bed with silky white linens and decorative blue accents. A blue ottoman sits at the foot of the bed, while a large TV is placed on a dark wood dresser. Natural light filters in through the nearby balcony doors.

5 out of 5 average rating, 11 reviews

Waterfront Coastal Retreat | Steps from LBK Beach

Family-friendly condo rentals

A modern living area is visible, showcasing a cozy gray sofa and a glass coffee table atop a patterned rug. The open kitchen features stainless steel appliances and a bright green accent wall. Natural light streams through a nearby window, enhancing the inviting space.

4.92 out of 5 average rating, 214 reviews

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

5 out of 5 average rating, 5 reviews

A heated swimming pool is set within a sunlit outdoor area, surrounded by tropical greenery. Comfortably arranged lounge chairs can be seen beside the pool, while a covered area with dining options is available underneath the balcony above.

Condo in Bradenton Beach

Lime Kiss A! 3 Bedroom, 2 Bathroom Home Just Acros

A welcoming living area features a green sofa adorned with colorful cushions. A large tropical mural displays flamingos and lush foliage. A round coffee table sits in front of the sofa, while a dining area with elegant chairs and a floral centerpiece is visible in the background.

4.86 out of 5 average rating, 200 reviews

♥ 1/2 mile to BEACH! ➸ KING in master ➸ POOL ♥

5 out of 5 average rating, 8 reviews

Spectacular 2B Condo on Siesta Key Beach

4.97 out of 5 average rating, 35 reviews

Charming Poolhouse · 1BR · Close to Siesta

4.93 out of 5 average rating, 28 reviews

Your Beachside King Suite Retreat!

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

4.9 out of 5 average rating, 206 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Palm thatched umbrellas provide shade over teal lounge chairs arranged on a sandy beach. The shoreline is visible in the distance, with clear blue skies overhead and beach equipment scattered in the background, enhancing a relaxed beach atmosphere.