Vacation rentals with outdoor seating 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, 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 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, 138 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.

5 out of 5 average rating, 129 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream A purpose-built luxury family vacation home designed by parents for unforgettable stays. Enjoy swing dining chairs, a glowing neon moss wall, backyard putt-putt, and a free heated saltwater pool (Nov 21–Apr 1st). 15 minutes to Siesta & Lido Key Beaches. ✔ Private heated saltwater pool ✔ Backyard mini golf & outdoor games ✔ Luxury covered lanai w/ high ceilings ✔ Super kid-friendly (toys, Pack ’n Plays) ✔ Jura Espresso Machine ✔ 65” Frame TV w/ YouTube TV

4.98 out of 5 average rating, 134 reviews

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.

Home in South Sarasota

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.

4.98 out of 5 average rating, 237 reviews

A clear view of the tranquil waters reveals a vibrant blue float anchored in the shallows. The backdrop features a picturesque beachside resort with palm trees, framed by a clear blue sky and soft sandy shorelines.

Condo in Longboat Key

Island Time on LBK!

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...!

4.98 out of 5 average rating, 110 reviews

Home in Bradenton Beach

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

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, 377 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, 120 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 Siesta Key outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

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, 156 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

An aerial view of Siesta Key displays a coastal neighborhood with a network of waterways. The vibrant blue water contrasts with the greenery and residential homes, highlighting the island's tranquil setting. The city skyline of Sarasota is visible in the distance, framing the picturesque scene.

4.99 out of 5 average rating, 102 reviews

Siesta Key Beach Getaway

4.85 out of 5 average rating, 110 reviews

Stylish & Bright: Steps to Beach ~ Pool ~ Hot Tub!

4.86 out of 5 average rating, 139 reviews

Home in Longboat Key

Summer House longboat key

A spacious kitchen area features sleek cabinetry and a large center island with a striking stone surface. Wooden beams add a rustic touch overhead, while modern appliances are seamlessly integrated. Natural light floods the space, creating an inviting environment for meal preparation and gathering.

5 out of 5 average rating, 4 reviews

Rustic Sands - 650

A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.

4.98 out of 5 average rating, 139 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

5 out of 5 average rating, 11 reviews

Siesta Key House, Pool & Hot Tub, 1 mile to beach

4.94 out of 5 average rating, 53 reviews

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

Home in Arlington Park

Private Heated Pool Retreat for Two Families

Apartment rentals with outdoor seating

4.85 out of 5 average rating, 295 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.

Apartment in Siesta Key

Siesta Key - Poolside Suite - Studio - Free kayaks

4.82 out of 5 average rating, 310 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.

Apartment in Siesta key

VILLA 5 · Pool view. King bed. Daily rentals

4.77 out of 5 average rating, 213 reviews

Apartment in Siesta Key

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

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.

Apartment in Sarasota

Come Enjoy Our Peaceful Retreat

4.84 out of 5 average rating, 122 reviews

A spacious sleeping area features a queen-size bed with a light blue patterned bedspread. A cozy armchair is positioned beside the bed, and window treatments allow natural light to brighten the room. Light wood flooring complements the neutral-toned walls.

Apartment in Lido Key

Lido Key FL Studio/Efficiency 5

4.91 out of 5 average rating, 113 reviews

A covered seating area is furnished with comfortable wicker chairs and lounge chairs featuring green cushions. Lush plants and palm trees enhance the outdoor space, while a view of the shared garden can be seen in the background. A book and a sun hat rest on a side table.

Apartment in Sarasota

Minutes to Siesta or DT w/heated pool and Hot Tub

Apartment in Holmes Beach

A spacious pool area is surrounded by palm trees and tropical landscaping. The clear blue water of the pool reflects the bright sky. Comfortable lounge chairs are positioned on the pool deck, inviting relaxation. A dining table is visible in the background, shaded by trees.

4.96 out of 5 average rating, 163 reviews

Cabin 1 at Spinnakers Vacation Cottages

4.99 out of 5 average rating, 106 reviews

A modern living area features a comfortable white sofa adorned with decorative pillows and a light-colored coffee table. A wall-mounted TV is positioned above a stylish console, while a cozy armchair and indoor plants add warmth. Soft lighting is diffused through natural daylight.

Apartment in Siesta Key

Modern Chic Getaway 2 Min. Walk to Beach & Village

Condo rentals with outdoor seating

4.92 out of 5 average rating, 157 reviews

Gulf Views | Walkable | Spacious

An aerial view captures the condo complex beside a private beach, with emerald waters and white sandy shores in the background. The surrounding area includes multiple pools and shaded lounges, highlighting the tranquil atmosphere of Siesta Key.

4.93 out of 5 average rating, 203 reviews

Bright and Beachy - Steps to the Water!

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.

4.89 out of 5 average rating, 141 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.

4.82 out of 5 average rating, 142 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

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.

4.84 out of 5 average rating, 141 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

4.99 out of 5 average rating, 173 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 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

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.