Holiday rentals with outdoor seating near Siesta Beach

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, 156 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 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, 324 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 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.

4.94 out of 5 average rating, 137 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.

A charming yellow home is set against a backdrop of palm trees, with a brick paved driveway leading to a two-car garage. Lush greenery surrounds the property, providing a sense of privacy and tranquility.

4.91 out of 5 average rating, 126 reviews

Siesta Key, FL - Casa Berano

Quiet, private home on lovely Siesta Key. 1.6 miles from lovely #1 Beach in the country. 1.9 miles to Siesta Key Village. FREE shuttle to village & beaches 7 days/wk. Private saltwater pool/enclosed lanai. Spacious 3bd/3b. Pets, dogs only, welcome, pls add to your total guest reservation. Open floor plan, large living area. Kitchen opens into living area & 2 dining areas w/large tables. 2 car gar. brick paved driveway, in home laundry. 6 Guests Max 2 pets max (dogs only), under 50lbs.

A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.

4.98 out of 5 average rating, 133 reviews

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

4.79 out of 5 average rating, 103 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.

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, 145 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!

The balcony features a cozy seating arrangement comprising two chairs and a coffee table, all set against a stunning ocean view. The turquoise waters and sandy beach are visible beyond the railing, offering a serene backdrop for relaxation.

4.99 out of 5 average rating, 105 reviews

6 Siesta Breakers - Condo, Ocean View, Heated Pool

Luxurious apartment style condo on Siesta Key Beach, Sarasota Florida overlooking the quartz white sand and turquoise waters of the #1 beach in the USA. Enjoy exquisite ocean views from the balcony or just a few steps to the beach. Our gated community positions you steps away from whatever your heart desires (pool, ocean, grocery store, restaurants, live music and local shops). Your options are limitless on Siesta Key. If you need more than one condo check - airbnb.com /h/breakers203

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, 376 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.

4.95 out of 5 average rating, 192 reviews

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. VR24-00265

A single-story tropical home is presented with a light blue exterior and a metal roof. Lush palm trees and colorful plants border the pathway leading to the entrance. An outdoor umbrella sits near the entry, enhancing the welcoming appearance of the property.

4.93 out of 5 average rating, 156 reviews

Siesta Key Beach & Village 2BR/2BA Steps to Beach

This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located in the heart of Siesta Key Village. You will be within a 2 minute walk to Siesta Key Beach and Siesta Village. With a beach house décor and equipped with 3 smart TVs, WIFI, cable, refrigerator, microwave, W/D, grill, beach chairs, toys for the kids, beach wagon, 1 queen bed, 2 twin beds and sleeper queen sofa. This private beach home has everything you need for a beach vacation. Local ownership.

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, 119 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.

Popular amenities for rentals with outdoor seating near Siesta Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.98 out of 5 average rating, 155 reviews

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

A spacious backyard is shown at sunset, featuring a heated pool surrounded by a tiled patio. Tropical palm trees frame the area, and a tiki bar can be seen in the background. Soft outdoor lights create a welcoming ambiance as the sky fills with vibrant orange and purple hues.

4.94 out of 5 average rating, 155 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

Superhost

5 out of 5 average rating, 3 reviews

Luxury 3B/3B waterfront home w/ pool + boat access

4.97 out of 5 average rating, 118 reviews

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

A private heated pool is surrounded by lush palm trees and a well-maintained lawn. An outdoor dining area with a large umbrella is visible, along with two lounge chairs positioned near the pool. The area is brightened by clear blue skies and sunlight.

5 out of 5 average rating, 159 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

4.96 out of 5 average rating, 25 reviews

Heated saltwater pool near Siesta and Downtown

A mid-century structure is set among lush palm trees, showcasing a combination of wooden accents and large glass windows. A curved gravel driveway leads to the front entrance, inviting natural light into the living areas and offering a serene outdoor landscape.

4.92 out of 5 average rating, 143 reviews

St Armand's Mid-Century Oasis

4.95 out of 5 average rating, 20 reviews

Bike to Beach Double King Suites, Pool & Mini Golf

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 175 reviews

A spacious living area is adorned with a light blue sofa and a comfortable armchair, complemented by a coffee table and decorative rug. A mounted TV is set against a striking blue accent wall, and natural light filters through sheer curtains, enhancing the coastal ambiance.

Flat in Siesta Key

Cozy Coastal Getaway 2 min Walk to Beach & Village

4.85 out of 5 average rating, 293 reviews

A bright blue entrance door labeled 'Poolside Suite' is visible, leading into the suite. The door is framed by a light blue exterior, with a view of the pool area and palm trees in the background. Sunlight casts gentle shadows on the patio.

Flat in Siesta Key

Siesta Key - Poolside Suite - Studio - Free kayaks

4.87 out of 5 average rating, 181 reviews

A modern studio layout features a queen bed with a blue floral bedspread, complemented by a comfortable futon and decorative pillows. A small dining table with two chairs is positioned near the seating area, while large blue curtains frame the window, allowing natural light to enter.

Flat in Sarasota

Chic & Cozy Getaway • Near Siesta Key Beach

4.98 out of 5 average rating, 187 reviews

A bright living area is viewed, showcasing a cozy sofa adorned with decorative pillows. Light drapes frame large glass doors that open to a vibrant garden patio. Two comfortable chairs and a wooden table complement the space, creating a welcoming atmosphere for relaxation.

Flat in Sarasota

Near Siesta Key Beaches - Quiet 1 BR apt

4.81 out of 5 average rating, 308 reviews

A shared pool area is surrounded by vibrant blue walls and tropical greenery. Lounge chairs in various colors are arranged around the pool, inviting relaxation. Bright sunlight reflects off the water's surface, enhancing the welcoming atmosphere of this outdoor space.

Flat in Siesta key

VILLA 5 · Pool view. King bed. Daily rentals

Superhost

Flat in Siesta Key

4.77 out of 5 average rating, 213 reviews

Cosy “Hide-A-Way Suite” Siesta Key Beach

5 out of 5 average rating, 101 reviews

The image captures a serene beach scene, showcasing gentle waves lapping at the shore under a bright blue sky. Tall grasses sway gracefully in the foreground, while lush greenery borders the sandy beach, leading to the calm, turquoise waters of the Gulf.

Flat in Longboat Key

Sandy Toes: Open Monday & Tuesday, $150/nt + Fees!

4.99 out of 5 average rating, 134 reviews

A cozy living room features a comfortable couch with decorative orange pillows. Bright, patterned curtains complement the colorful rug and a wooden coffee table. Large windows allow natural light into the space, while a television is positioned against a cheerful yellow entertainment unit.

Flat in Sarasota

Come Enjoy Our Peaceful Retreat

Apartment rentals with outdoor seating

A spacious bedroom features a modern white bed with plush pillows and a decorative brown pillow. A mirrored closet reflects the elegantly decorated space, which includes a stylish bedside table and soft lighting from a lamp. Natural light filters through the vertical blinds.

4.92 out of 5 average rating, 118 reviews

The Honeymoon Suite 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.

4.82 out of 5 average rating, 141 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

4.98 out of 5 average rating, 125 reviews

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

4.97 out of 5 average rating, 147 reviews

The bedroom features a spacious bed with decorative pillows and a light blue throw. An accent bench sits at the foot of the bed, while a round mirror reflects soft lighting from a chandelier. A patterned wallpaper adds a coastal touch, enhancing the serene ambiance.

Apartment in Bradenton

KING Bed + Anna Maria Island Beaches + Beach Gear!

Apartment in Bradenton Beach

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.

4.99 out of 5 average rating, 173 reviews

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

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, 117 reviews

Perfect Location in Siesta Key

A three-story condominium building is shown, featuring a combination of palm trees and lush green landscaping at the forefront. Balconies are visible on each level, with a red-tiled roof adding a distinct character to the architecture.

4.96 out of 5 average rating, 115 reviews

Seaside on Siesta Key Beach

A private outdoor patio is highlighted, featuring a round table surrounded by four chairs. A large blue umbrella provides shade, while tropical greenery adds a natural backdrop. Paved brick flooring completes the inviting outdoor space, ideal for relaxation.

4.92 out of 5 average rating, 226 reviews

Steps to Beach & Siesta Key Village-Village condo

Other holiday rentals with outdoor seating

An aerial view captures a vibrant Siesta Key neighborhood, showcasing well-maintained homes amidst lush palm trees. The crystal-clear waters and white sandy beaches are visible in the distance, alongside the coastline dotted with beachgoers. Nearby, a mix of buildings emphasizes the area’s charm and accessibility.

4.97 out of 5 average rating, 59 reviews

Beach Rd, 300ft to Beach Access & 500ft to Village

Superhost

5 out of 5 average rating, 4 reviews

Direct Gulf View - Residence 603

4.97 out of 5 average rating, 79 reviews

A serene bedroom featuring a spacious bed with light bedding. Natural light pours in through two windows, illuminating the room's wooden beams and soft green paneling. A small table with a lamp and decorative items completes the inviting space.

Home in Myakka City

"Little Siesta" - Farm home near Terra Nova

5 out of 5 average rating, 8 reviews

Bungalow in Sarasota

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay

Luxe

5 out of 5 average rating, 11 reviews

Mid-Century Modern, Pool, Mins to Siesta Key Beach

A curved swimming pool is set against a backdrop of lush tropical foliage and palm trees, with water views extending to a nearby dock. Brightly colored pots with plants are placed around the pool area, enhancing the serene outdoor setting.

4.96 out of 5 average rating, 79 reviews

True Island Living House/beach/water views

A serene outdoor area features a heated saltwater pool surrounded by a screened enclosure. Two lounge chairs are positioned under an umbrella, while lush greenery adorns the perimeter, creating a calming atmosphere at sunset.

5 out of 5 average rating, 66 reviews

Walk to Siesta Village, Heated Saltwater Pool