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, 167 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

4.96 out of 5 average rating, 110 reviews

Sun-filled cottage with pool, walk to beach

Welcome to Palm Cottage. Our space is the perfect cozy getaway for any time of year. Recently renovated three bedrooms and one bathroom make this the perfect spot for two couples or a family. The private backyard includes a brand new pool with a hot tub and a sun shelf, as well as outdoor dining area and fire table. Enjoy a leisurely stroll to Siesta Key to play at the beach or grab a meal at one of the many restaurants. Home includes two bikes and all the gear you need for a day at the beach.

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, 145 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!

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, 145 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!

4.95 out of 5 average rating, 196 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. *Brand new pool* VR24-00265

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, 156 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 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, 166 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 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, 131 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.

A spacious bedroom features a large king-size bed dressed in neutral linens. A flat-screen television is mounted on the wall, while natural light enters through sliding glass doors. A small table and a decorative plant add a touch of elegance to the minimalist decor.

4.82 out of 5 average rating, 349 reviews

[Beach Elements] pool view + private beach & bikes

Relax & Recharge at Siesta Beach in a poolside one-story villa. +2 beach cruiser bikes ( $40 each per stay) NEWLY REMODELED!! King size bed + queen sofa bed This modern studio is fully equipped with a kitchen, granite countertops & stainless steel appliances. King size bed and full-size sleeper sofa. Recently updated kitchen, bathroom, and a complete living area. It overlooks 1 of 3 pools Enjoy the morning sun, with your coffee on the patio.

An open concept living area features a blend of modern and comfortable furnishings. A dark wooden coffee table is centered on a textured rug, with a stylish mirror and a ceiling fan overhead. Large glass doors allow natural light and views of the screened Florida Room.

4.91 out of 5 average rating, 102 reviews

Enchanting Coastal Ambiance & Breathtaking Sunsets

Welcome to your slice of paradise! Our stunning vacation rental offers the ultimate beachside getaway, providing you with a luxurious and unforgettable experience right on the main strip of the world-renowned Siesta Key Beach and the vibrant Siesta Key Village. The apartment or best referred to as CasaPlaya, features open concept living, a chic kitchen, fully upgraded bathroom and screened in Florida Room for your enjoyment.

4.85 out of 5 average rating, 170 reviews

Townhouse in Siesta Key

Luxury Siesta Key Compound | Pool | Walk to Beach

Luxury Beachside Retreat ✨🌊 Just steps from Siesta Key’s Public Beach, this 1,850 sqft 3BR/2.5BA townhouse offers 2 king bedrooms and a romantic loft with queen bed, private balcony + stunning Gulf views. Max. 6 guests. All 3 balconies overlook the beach. Enjoy a heated lagoon pool (shared by only 2 duplexes), free Wi-Fi, beach chairs, umbrellas & parking for 2–3 cars. The best location for your Siesta Key escape!

A living area is depicted with a neutral color palette and light hardwood flooring. A blue sofa and a wooden coffee table sit in front of a television on a console. A dining area with a table and chairs is visible in the background, alongside large sliding doors leading to an outdoor space.

4.94 out of 5 average rating, 132 reviews

Siesta Beach home w/ private access, walk to town!

Welcome to your own private getaway directly on Siesta Beach! Meticulous, updated unit with amazing location to the village and access to tow You will literally, walk out your door, down the steps, 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 bedroom 3 bathroom beachfront home with Gulf views that sleeps 8.

Popular amenities for rentals with outdoor seating near Siesta Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.

5 out of 5 average rating, 103 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

5 out of 5 average rating, 8 reviews

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

5 out of 5 average rating, 11 reviews

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

4.97 out of 5 average rating, 39 reviews

Luxury Canal-Front Home + Heated Pool Near Beach

4.95 out of 5 average rating, 42 reviews

Modern Home Heated Pool near Siesta & Downtown

5 out of 5 average rating, 112 reviews

The Blessing House- Htd Pool/Spa, Close to Beaches

An aerial view captures the beachfront property nestled among greenery, with sandy pathways leading to the beach. The top floor condo is highlighted, surrounded by other buildings, while the striking blue Gulf waters stretch in the background, meeting the clear sky.

5 out of 5 average rating, 46 reviews

Beachfront 180-Degree View, Walk to Village!

A spacious backyard features a heated private pool surrounded by a paved area. Lounge chairs are positioned around the pool, with umbrellas providing shade. Lush greenery and a fence frame the yard, creating a serene outdoor setting, ideal for relaxation.

4.8 out of 5 average rating, 131 reviews

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 190 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

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.

4.98 out of 5 average rating, 191 reviews

Near Siesta Key Beaches - Quiet 1 BR apt

4.8 out of 5 average rating, 325 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

5 out of 5 average rating, 117 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

Beach Bliss: Open Monday, $250/nt + Fees!

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.

4.84 out of 5 average rating, 138 reviews

Lido Key FL Studio/Efficiency 5

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.

4.88 out of 5 average rating, 124 reviews

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

4.87 out of 5 average rating, 308 reviews

An open living space features a fully equipped kitchen with wooden cabinetry, a dining table, and seating area. A flat-screen TV is mounted on the wall. Light-colored flooring enhances the spacious feel, while natural light brightens the room through multiple windows.

Flat in Siesta Key

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

A spacious bedroom is featured, with a large bed dressed in neutral linens. A ceiling fan and mounted flat-screen TV are visible. Bright light enters through multiple windows, illuminating the open-concept area that leads to a kitchenette and bathroom.

4.88 out of 5 average rating, 173 reviews

Luxury King Suite just steps to Siesta Key Beach

Apartment rentals with outdoor seating

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, 204 reviews

Bright and Beachy - Steps to the Water!

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

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, 388 reviews

On the Beach; Siesta Key SunBum Studio

4.98 out of 5 average rating, 130 reviews

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

A dining table is set with elegant glassware and neutral tableware. A decorative figurine of a crane stands between two tall candlesticks, with a soft ocean view visible through the screened lanai in the background.

4.92 out of 5 average rating, 102 reviews

Siesta Key Oasis with Gulf Views

A spacious bed is dressed with a white quilt and complemented by two golden yellow pillows. Neatly stacked white towels are placed at the foot of the bed. A piece of artwork depicting a beach scene hangs above the bed, with natural light streaming through a window nearby.

4.78 out of 5 average rating, 124 reviews

Siesta Key Walk to Beach Condo

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, 126 reviews

Perfect Location in Siesta Key

4.79 out of 5 average rating, 107 reviews

Beachwalk Townhouse with view of Gulf of Mexico

Other holiday rentals with outdoor seating

5 out of 5 average rating, 3 reviews

The Siesta Key Retreat - An Island Garden Oasis!

5 out of 5 average rating, 11 reviews

3 bed, 4 bath, private pool home, steps to beach

4.77 out of 5 average rating, 13 reviews

Home in Anna Maria

South Bay Beach House:Bay Front Luxury Beach Villa

An aerial view captures the vibrant landscape of Siesta Key, showcasing a blend of colorful buildings and lush greenery. The shoreline with crystal clear waters and sandy beaches extends in the background, illustrating the proximity to the vacation rental. The scene reflects the lively, serene atmosphere of the area.

4.95 out of 5 average rating, 64 reviews

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

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.

4.81 out of 5 average rating, 62 reviews

Beach Front Haven

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, 5 reviews

Rustic Sands - 650

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.

4.94 out of 5 average rating, 79 reviews

1 Bed Cottage, Full Remodel, Beach Access #7, Walk

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.