Holiday rentals with outdoor seating near Siesta Beach

4.99 out of 5 average rating, 201 reviews

A covered patio space is surrounded by lush greenery and decorative plants. A light-colored table and two chairs are arranged on a tiled floor. Large, double doors in a vibrant blue lead to the outdoors, enhancing the welcoming atmosphere.

Guest suite in Sarasota

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

An inviting fire pit is surrounded by a circular stone seating area, featuring two Adirondack chairs. Decorative cushions add color to the seating. A spacious, fenced backyard is complemented by a serene evening sky with pastel hues.

4.97 out of 5 average rating, 102 reviews

Cottage w/Fire Pit Near Siesta!

Welcome to "Polka Dotted Pelican" located just a stone’s throw from world famous SIESTA KEY! This charming cottage is completely remodeled & nestled in a quiet neighborhood. Enjoy roasting s'mores around the INCREDIBLE backyard fire pit!! The living area opens to a large covered lanai for outdoor dining & relaxation. Comfortable, clean, & fully equipped! Amenities include high speed Wi-Fi, dedicated workspace, free indoor laundry, & bikes/games/beach chairs. Walk or bike to nearby Gulf Gate.

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.

5 out of 5 average rating, 110 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!

4.96 out of 5 average rating, 126 reviews

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.

Apartment in Sarasota

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 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, 134 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

4.8 out of 5 average rating, 121 reviews

A bright sleeping area features a spacious bed with a blue and white patterned blanket. Large sliding glass doors lead to an outdoor area with a pool, framed by greenery. A flat-screen TV is mounted on the wall opposite the bed.

Flat in Siesta Key

Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool

Kick back, relax & enjoy Siesta Key! Brand newly remodeled in Sept 22 this studio sleeps 4 people in 2 queen beds side by side. Located in “Solitude Suites on Siesta Key” resort, this Waterview Suite is sure to please you! Enjoy your ground floor studio with a kitchenette, and full bathroom. Right outside your door is the resort with shared access to: the community pool, Tiki hut with ping pong table, bbq grills, and the boat dock with free kayaks & SUPs for your use! Max 4 occupants.

5 out of 5 average rating, 19 reviews

Bungalow in Siesta Key

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. Featuring a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed and private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. An additional queen sofa-bed allows accommodations for three guests.

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.

4.95 out of 5 average rating, 103 reviews

Seaside on Siesta Key Beach

Seaside on Siesta is the perfect walkable location to everything you need for a seaside getaway! Located directly across the street Siesta Key Beach. NEWLY RENOVATED in 2025. Walk or take the FREE trolley (trolley stop located feet from our front patio) to Siesta Key Village. First floor unit so no need to wait on elevators. The spectacular white quartz beach and crystal clear water awaits you just outside your door! Search "Seaside on Siesta Tour" on Youtube for a video tour.

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, 347 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. Enjoy 2 free bikes day rental with booking!

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.

4.96 out of 5 average rating, 112 reviews

Palm Bay Club! Resort Style 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.

A living area features a comfortable green sofa complemented by a lamp casting a warm glow. A white wicker chair adds a coastal touch, positioned beside a small white table. Light wooden floors extend across the space, with soft wall art and a wall-mounted TV enhancing the environment.

4.85 out of 5 average rating, 252 reviews

Cozy 1BR Beach Condo on Siesta Key!

Experience the best of both worlds in this beautiful bayside 2nd floor unit! Sea Club II offers the charm of Old Florida with its shell driveway and old oak and palm trees throughout the property. Relax by the upgraded bayside pool or enjoy Happy Hour by the Tiki Hut or on the open lawn and watch the boats (BIG and small) pass by on the intercoastal. Grills are available for guests to use by the pool area. We also have a new fishing pier and boat dock.

The exterior of the duplex presents a welcoming entrance with a covered front porch and seating. Lush greenery and small potted plants enhance the home's facade. The driveway is visible, leading to the well-maintained lawn and fenced backyard area.

4.94 out of 5 average rating, 105 reviews

1 Bed 1 bath 7 mins to the beach

This charming 1 bedroom 1 bath space has a calming coastal vibe with dedicated driveway parking, front porch, and fenced backyard. This unit is newly renovated and furnished, and is part of a duplex with a large shared backyard. It is within walking/biking distance or a short drive to grocery stores and restaurants, and 7 mins to Siesta Key - FL's #1 beach! Longboat Key, St. Armands, Turtle Beach, and Downtown are all a short drive away!

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 private backyard is illuminated with string lights in the evening. A fire pit table with a glass barrier features dancing flames, while a hammock is visible to the side. The space includes lounge seating with turquoise cushions, creating a relaxed outdoor atmosphere.

4.91 out of 5 average rating, 158 reviews

Quiet Retreat-5mi to Beach-Hot Tub, Outdoor Shower

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, 140 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

4.97 out of 5 average rating, 257 reviews

Your private retreat near Siesta Key Beach.

A light-filled living area features a comfortable sofa, a wooden coffee table, and a dining space with a round table and chairs. The kitchen is equipped with modern appliances and cabinetry, while beach-themed decor adds a casual touch to the environment.

4.98 out of 5 average rating, 178 reviews

New remodel- 150 Yds to Beach and Restaurants!

A private courtyard featuring a heated pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned beside the pool, and a small fountain adds a soothing element. A cozy seating area is visible near the entrance to the adjoining building.

4.94 out of 5 average rating, 127 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.94 out of 5 average rating, 108 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

4.94 out of 5 average rating, 118 reviews

Home in Holmes Beach

The Peachy Beach House, steps to the gulf

A bright and airy indoor space features a coastal-themed rug with a starfish design. Light-colored furniture and a wooden table provide a casual dining area, while large windows allow natural light to fill the room and offer views of the backyard.

4.93 out of 5 average rating, 376 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

Apartment rentals with outdoor seating

A serene community pool is surrounded by a fence and complemented by lounge chairs positioned nearby. The pool's clear blue water reflects the sunlight, while the yellow exterior of the building provides a warm backdrop. Windows with awnings complete the inviting atmosphere of the area.

4.94 out of 5 average rating, 157 reviews

December Special! First 3 weeks only $150/night!

A well-organized kitchenette is presented, featuring a microwave, sink, and open shelving with various containers and glassware. The blue walls enhance the workspace, while a polished wooden countertop reflects ample light from the surroundings.

4.81 out of 5 average rating, 114 reviews

Cozy and Private Studio Near Downtown & Beaches

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, 179 reviews

Near Siesta Key Beaches - Quiet 1 BR apt

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.

4.89 out of 5 average rating, 168 reviews

Chic & Cozy Getaway • Near Siesta Key Beach

A private entrance is framed by a sleek plant and modern features. The entrance door is flanked by a wall light and a smooth concrete pathway, complemented by potted plants that enhance the outdoor space.

4.97 out of 5 average rating, 176 reviews

Gillespie On The Park, Walk to Downtown

4.76 out of 5 average rating, 208 reviews

An open-concept living space features a modern kitchen with white cabinetry and stainless-steel appliances. A cozy seating area with light-colored sofas is complemented by a decorative rug. Large windows allow natural light to fill the room, providing views of the outdoor patio.

Flat in Siesta Key

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

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.

4.98 out of 5 average rating, 128 reviews

Come Enjoy Our Peaceful Retreat

A spacious bed with a white coverlet is flanked by two nightstands featuring soft lighting. Decorative pillows rest atop the bed, and a tasteful piece of wall art adds a touch of color to the neutral backdrop.

4.85 out of 5 average rating, 219 reviews

Updated Old Florida Studio Getaway in Central SRQ

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 118 reviews

A spacious living area is highlighted by a light-colored sectional sofa adorned with colorful pillows. A large coffee table is positioned in front of the sofa, and a dining table with six chairs is visible in the background. A fan hangs from the ceiling, and natural light enters through nearby windows.

Apartment in Sarasota

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

4.97 out of 5 average rating, 123 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!

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, 330 reviews

[Beach Elements] pool view + private beach & bikes

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, 155 reviews

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

4.85 out of 5 average rating, 131 reviews

A modern living area features a blue sofa with decorative pillows and a low coffee table. A dining set with white chairs is visible in the background. Bright natural light filters through sheer curtains, enhancing the neutral grey walls and stylish artwork.

Apartment in Sarasota

Anchor house +6 min. from Siesta Beach+heated pool

4.91 out of 5 average rating, 137 reviews

A fire table is positioned in view of a vibrant sunset, reflecting shades of orange, pink, and purple across the sky. The scene is framed by large glass panels, offering unobstructed views of the horizon, enhancing the outdoor experience.

Apartment in Bradenton

New Luxury 3/3 Condo in Margaritaville Resort

Apartment in Longboat Key

4.98 out of 5 average rating, 217 reviews

Oceanfront Mid-Island on LBK Open Tomm-TU $175/nt!

A contemporary living area features a comfortable gray sofa with decorative pillows. A white coffee table sits centrally, while an accent chair with a colorful pattern offers additional seating. Two lamps illuminate the space, complementing the soft green walls.

4.85 out of 5 average rating, 158 reviews

The Key to a Great Vacation!

Other holiday rentals with outdoor seating

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.

4.92 out of 5 average rating, 72 reviews

Enchanting Coastal Ambiance & Breathtaking Sunsets

A serene outdoor space features a sparkling pool surrounded by lush greenery. Comfortable seating is provided under a large umbrella, while decorative light fixtures enhance the ambiance. Tropical plants and well-maintained landscaping create a refreshing atmosphere for relaxation and enjoyment.

4.98 out of 5 average rating, 88 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

5 out of 5 average rating, 15 reviews

A private heated pool is surrounded by a spacious stone patio, featuring comfortable lounge chairs. Lush greenery provides a tropical backdrop, while a charming cottage with turquoise siding is visible nearby. Soft sunlight reflects on the tranquil water, enhancing the peaceful ambiance of this outdoor area.

Home in Siesta Key

Toes In The Sand | Private Pool, Walk to Beach!

4.99 out of 5 average rating, 92 reviews

An airy dining area features a glass table supported by a unique wooden base, surrounded by four woven chairs. Natural light floods the open space, highlighting the modern kitchen with white cabinetry and high-end finishes, while a large pendant light adds a stylish touch.

Home in Siesta Key

Luxurious Private Retreat - Your Siesta Key Oasis!

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, 50 reviews

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

A heated pool is surrounded by lush greenery, with clear blue water inviting relaxation. Sunlight glimmers on the surface, and a cozy pool area is visible alongside a white two-story building. The space features a kayak resting against the pool's edge.

5 out of 5 average rating, 73 reviews

Beechwood Suites A

4.98 out of 5 average rating, 88 reviews

Sarasota Quiet & Clean Tiny Studio Apt

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.