House rentals near Lido Key Beach

A dining area features a wooden table surrounded by six chairs with patterned cushions. A fireplace is located on a white brick wall, while an open kitchen is visible in the background. Bright lighting enhances the airy feel, complemented by wood beamed ceilings.

4.97 out of 5 average rating, 101 reviews

Lido Beach Dream

Bright and sunny remodeled and updated beach home featuring wood beamed ceilings, new bamboo wood firs, with 3 good size bdrms, 2 full baths, , master with with en suite, 2 queen beds, 2 twin beds,open and airy kitchen w/ eating bar and table to seat 6 plus , new appliances, w/d, large family rmwith fireplace, huge year round air conditioned lanai, garage. Golf, sailing, walking & bike trails. Walk to St Armand's Circle, beach, heated pool block away, restaurants, 130 stores and spec. shops.

5 out of 5 average rating, 117 reviews

Living The Dream - Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream! From the swings at the dining room table and the neon sign, to the moss wall and the private putt-putt course, Living the Dream is fully loaded and is the ultimate luxury vacation home! Located just 15 minutes away from both Lido Key and Siesta Key Beach, the stay includes: ✔ Backyard Putt-Putt Course ✔ Saltwater Heated Pool - heated at NO extra cost from Nov 21 - April 1st ✔ Super Kid Friendly ✔ Jura Espresso Machine ✔ 65" Frame TV w/ Youtube TV Included

A quaint cottage features a vibrant red door, framed by lush greenery and colorful plants. The path leading to the entrance is bordered by neatly arranged brick landscaping, enhancing the inviting entrance to the home.

4.98 out of 5 average rating, 134 reviews

The Sweet Spot! Walk to DT & Free Trolley to Beach

Looking for the Sweet Spot in Sarasota? Look no further! This artistically updated cottage, nestled in the quiet, historic downtown neighborhood of Laurel Park is a just a short walking distance to some of the best downtown dining, shopping, arts venues and the renowned Selby Gardens. Take the free Breeze Trolley to Siesta Key and Lido beach. Relax in the private outdoor courtyard. It's is the perfect place for a couple's getaway, a family vacation, or a long term stay. So book now and welcome!

A private heated pool is enclosed by a screened lanai, surrounded by lush tropical plants. Soft purple lights create a relaxed ambiance. Comfortable seating and dining areas are positioned nearby, inviting leisurely moments by the water.

4.97 out of 5 average rating, 162 reviews

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

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!

A living area features wooden flooring with a large area rug at the center. Two gray armchairs are positioned near a media console, which supports a flat-screen television. Natural light is provided by windows adorned with sheer white curtains, and a green plant adds a touch of greenery.

4.95 out of 5 average rating, 520 reviews

The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

The outdoor area features a uniquely shaped heated saltwater pool with clear blue water. Surrounding the pool are loungers placed on a bright, white deck, complemented by tropical plants and palm trees that enhance the tranquil environment.

4.98 out of 5 average rating, 106 reviews

Tropical Oasis Heated Pool Hot Tub Near Siesta Key

Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!

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, 126 reviews

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

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

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.

5 out of 5 average rating, 34 reviews

Sarasota Escape | Minutes to Beaches + Downtown

HEATED POOL + ECO FRIENDLY. Relax with the whole family or bring that group chat trip to life at this peaceful retreat in the heart of Sarasota. Boasting a spacious and nature-inspired design, this home is a short drive to several world class beaches, the downtown Sarasota arts district, 5 star dining, shopping and more. The home is also located within walking distance of a park complete with playground, public pool, tennis + basketball courts, workout area and walking trails.

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

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

A private outdoor area is highlighted by a heated pool and spa, surrounded by a screened enclosure. Comfortable loungers and dining seating are present on the patio, with umbrellas offering shade. The tranquil blue water reflects the evening sky and palm trees in the background.

5 out of 5 average rating, 6 reviews

Seabreeze Serenity: Lido Key Poolside Paradise

Exclusive Amenities Include: • Private Heated Pool • In-ground spa • 3 Bedrooms, 2 Full Bathrooms • 2 King Beds & 2 Twin Beds, Sleeper Sofa (Sleeps 8) with linens provided • Spacious Outdoor Lounging Area • Free WiFi & HDTV’s • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs, Cooler, & Caddy Provided • Gas Grill

A private pool is surrounded by lush tropical foliage, creating a serene atmosphere. A waterfall feature can be seen cascading into the clear water. Colorful plants, including vibrant bougainvillea, enhance the natural beauty of the outdoor space.

5 out of 5 average rating, 30 reviews

Walk to Lido Beach &St. Armands -grill/HEATED POOL

A piece of paradise! Walk one block to the beach, 5-minute walk to St. Armands! HEATED POOL, 2BR w/grill. This beautiful home, nestled on a little piece of paradise, is just a stone's throw from Lido Beach! A perfect place to relax, unwind and enjoy your private, mature lush surroundings. This charming home has incredible internet, with 457 mbps download and 28 mbps upload speeds. It also has crown moldings and four ceiling fans.

Popular amenities for house rentals near Lido Key Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 87 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

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, 139 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

Superhost

Home in Longboat Key

4.85 out of 5 average rating, 131 reviews

Summer House longboat key

Superhost

5 out of 5 average rating, 3 reviews

Modern Home Near Downtown SRQ & Siesta Key Beach

4.94 out of 5 average rating, 117 reviews

Home in Holmes Beach

The Peachy Beach House, steps to the gulf

5 out of 5 average rating, 87 reviews

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

Superhost

5 out of 5 average rating, 4 reviews

Hidden Gem, Pool, Steps to Beach and St Armands

5 out of 5 average rating, 6 reviews

An inviting living area features a spacious sectional sofa adorned with vibrant pillows and a cozy fireplace. Large glass doors provide natural light and views of the outdoor pool area, while a unique coffee table complements the mid-century modern design.

Home in Siesta Key

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

Weekly house rentals

4.94 out of 5 average rating, 16 reviews

Pineapple House Near SRQ Downtown 15 Min to Beach

A single-story house is presented, featuring a light-colored exterior and a charming blue front door. A spacious driveway leads up to the garage. Palm trees and other greenery frame the entrance, contributing to a welcoming curb appeal.

4.92 out of 5 average rating, 39 reviews

Special price for 2025, read description

5 out of 5 average rating, 44 reviews

Sarasota Sunshine House with Heated pool & E-bikes

An inviting entrance showcases a bright living space visible through large glass doors. Light wood flooring and soft blue furnishings are seen, while a television is mounted on the wall. Lush greenery outside adds a touch of nature to the welcoming atmosphere.

4.91 out of 5 average rating, 33 reviews

Historic Downtown Sarasota - Gem II

A bright living area features a spacious white sofa centered beneath a large woven light fixture. Tropical plants are situated near large windows that allow natural light to fill the space. A neutral rug complements the light-colored furniture and decor.

4.93 out of 5 average rating, 27 reviews

Coastal Retreat near Siesta Key Beach and Downtown

A private entrance features a white fence and gate with the number 1825 displayed prominently. The pathway is paved with bricks and flanked by lush greenery and colorful flowers, leading to the home's inviting entrance.

5 out of 5 average rating, 19 reviews

The Gecko Bungalow - DT Sarasota

A spacious living area features a comfortable light-colored sofa complemented by a vibrant blue accent chair. The floor showcases a bold black-and-white rug, while artwork adorns the walls. A side table with a lamp is visible, creating an inviting atmosphere for relaxation.

4.91 out of 5 average rating, 53 reviews

Ben's Bungalow | 8 min to Siesta Key | Giga Wifi

The living area features a light-colored sectional sofa adorned with decorative pillows, paired with a wooden coffee table. A flat-screen TV is positioned on a media unit, while a dining table for six is visible in the background, alongside large windows allowing ample natural light.

4.97 out of 5 average rating, 62 reviews

Chasing the Sun Lido Beach House

Private house rentals

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, 77 reviews

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

A clear swimming pool reflects the evening sky, surrounded by a spacious patio. Outdoor seating for dining is arranged under an umbrella, with chairs positioned nearby. Lush greenery provides privacy, and large glass doors lead to the inviting interior of the home.

5 out of 5 average rating, 11 reviews

Pool, Spa, & Private Gym in the Heart of Sarasota

A serene pool area features a rectangular swimming pool surrounded by a spacious deck. Lounge chairs are positioned for relaxation, while lush greenery and a wooden fence provide privacy. A decorative statue adds an elegant touch to the tranquil environment.

4.99 out of 5 average rating, 94 reviews

The Oasis

A bright and airy living area features a sleek white sectional sofa with decorative pillows. A dark coffee table is centered in front, adorned with two gold vases. Framed art pieces are arranged on the wall, adding a touch of elegance to the space.

4.95 out of 5 average rating, 77 reviews

Siesta Key Escape-8 min to the beach,Spa,Bikes,BBQ

A well-lit bedroom features a spacious bed with a light-colored bedspread. Two large windows offer views of the outdoors, framed by sheer curtains. A ceiling fan hangs above, providing airflow. A comfortable chair and a dresser add practical elements to the inviting space.

5 out of 5 average rating, 11 reviews

The Palms Away

5 out of 5 average rating, 20 reviews

Luxury Sport Vacation Pool House-Downtown Sarasota

An open living space features warm wooden floors and large windows that provide ample natural light. A circular dining table is surrounded by six wire chairs. A modern chandelier hangs above the table, while a comfortable chair is positioned nearby, creating an inviting gathering area.

5 out of 5 average rating, 30 reviews

Sanctuary by the Sea

A large screened pool area showcases a heated swimming pool surrounded by elegant marble tiles. Comfortable seating arrangements are visible on one side, with modern lighting suspended overhead. Lush greenery is present in the background, contributing to a serene outdoor space.

5 out of 5 average rating, 16 reviews

Poolside Paradise

Pet-friendly house rentals

A private pool is surrounded by a spacious patio with paver stones, offering an inviting area for relaxation. Several lounge chairs and a small table with decorative seating are positioned near the water. Lush greenery borders the yard, enhancing the secluded feel.

4.77 out of 5 average rating, 112 reviews

Pool house by the bay

A newly constructed cottage is showcased, featuring a clean white exterior complemented by a bright blue door. Lush green grass surrounds the property, adding a refreshing touch. A paved pathway leads to the entrance, with tall trees providing shade in the background.

4.77 out of 5 average rating, 148 reviews

Downtown New Construction House

A spacious screened-in pool area features a bright blue pool alongside lounge chairs. Strings of lights illuminate the space as the sunset casts a warm glow. Lush greenery surrounds the area, providing a tranquil setting for relaxation and entertainment.

5 out of 5 average rating, 16 reviews

Salt Water Heated Pool|Arcade Games|Game Room

The spacious backyard features a heated pool illuminated with purple lighting, surrounded by lounge chairs and umbrellas. A dining table for eight sits nearby, with a cozy fire pit area providing evening ambiance. Pool floats are present, enhancing recreational options.

4.97 out of 5 average rating, 33 reviews

Luxe Oasis Mins to Beach & Downtown w/Heated Pool

An outdoor dining area is displayed, featuring a large black table surrounded by six black chairs. An oversized turquoise umbrella offers shade, and a grassy backyard is visible in the background, accented by palm trees and lush greenery.

4.97 out of 5 average rating, 89 reviews

Paradise Retreat Bring Family to the Beach!

A serene saltwater pool features a spa section, adorned with colorful inflatable floats. Lush greenery surrounds the pool area, enhancing the tranquil outdoor space, with a clean, modern stone deck complementing the vibrant tile accents.

5 out of 5 average rating, 87 reviews

Modern Organic King Beds Salt POOL/SPA SRQ Escape

A private outdoor space is presented, featuring a heated saltwater pool illuminated by soft lighting. A hammock is hung nearby under a stylish frame, surrounded by lush greenery and a fenced area, enhancing the serene ambiance for relaxation.

4.96 out of 5 average rating, 111 reviews

The Wisteria Oasis W/swings, heated pool & hot tub

A handcrafted wooden pelican figurine stands prominently on the countertop, adding a coastal touch. Above, pendant lights hang beneath a bamboo ceiling, providing a warm glow. The background reveals glimpses of a colorfully decorated space with various shelves and artwork.