House vacation rentals in Osprey

4.97 out of 5 average rating, 143 reviews

Near Siesta Key Pet Friendly Sarasota Retreat.

Escape to this beach inspired bungalow with a fully equipped kitchen and a fenced yard to relax in the sunny outdoors. Only 10 minutes to Siesta Key Beach! Enjoy the Sarasota beaches, museums, parks and downtown Sarasota, all just minutes away. Centrally located to grocery stores and restaurants. From coastal decor to comfortable beds, every part of your experience was thoughtfully curated by the owners to allow you to sit back, so feel free to put your feet up and relax at Barefoot Bungalow,

A serene lake mirrors the surrounding landscape, showcasing greenery and trees along the shoreline. The cloudy sky is reflected in the still water, creating a calming ambiance. The scene emphasizes the natural beauty and tranquility of the property.

4.73 out of 5 average rating, 351 reviews

The Ibis Cottage

Freshly renovated, The Ibis Cottage is a cozy studio on a beautiful property overlooking a small lake. It is a 5 minute drive to Nokomis Beach, Siesta Beach and Venice Beach are within easy reach, and a block away to the Legacy Trail bike path (Sarasota to Venice). Enjoy seeing a variety of birds on the property including the ibis, heron, and snowy egret. The cottage is conveniently located between Sarasota and Venice. The perfect location for enjoying the Gulf coast and outstanding beaches.

A light-filled entryway features a wall of glass shelving with decorative items. Double glass doors provide access to the outdoor space, which is partially visible through the glass. A small mat lies on the floor near the entrance.

4.91 out of 5 average rating, 213 reviews

Sunshine Suite, Minutes to Beach,Tropical Paradise

The Sunshine Suite.Lots of natural light in this totally updated modern 3 bed/1 bath home.It is a completely separate dwelling w separate entry from the other dwelling on the property sharing no common walls. Smart thermostat & door lock. Keyless entry.Brand new AC, gas oven, quartz counter w/ custom marble backsplash, modern & comfortable furniture, private outdoor area, gas BBQ grill, off street parking.Great location! Minutes to Siesta Key beach, shopping/UTC, interstate, hospital & downtown

An outdoor seating area features a rectangular table surrounded by four chairs, all set on a patterned rug. Two cushioned lounge chairs are positioned beside a large umbrella. A BBQ grill and greenery are visible in the spacious, fenced backyard.

4.96 out of 5 average rating, 104 reviews

Beachside Bliss: Family Home-Siesta Key-3BR2BA

Escape to this stunning, fully renovated 3BR/2BA home in the prestigious Gulf Gate Neighborhood, just 5 minutes from Siesta Key Beach – ranked the #1 beach in the U.S.! This spacious and airy retreat is designed for relaxation and making unforgettable memories. Enjoy an impeccably styled interior, modern amenities, and a prime location close to Sarasota’s best attractions. Indulge in top-rated restaurants, vibrant shopping centers, and endless beachside adventures—all just around the corner.

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, 108 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, 115 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 vibrant sunset lights up the sky in shades of orange and pink, framed by tall trees that line a quiet street. The silhouettes of palm trees add to the tropical ambiance, while homes are visible in the background, nestled among the lush landscaping.

4.92 out of 5 average rating, 102 reviews

Spectacular Sunsets! 15 min Siesta Key!

This villa is spacious and bright with lots of windows. The interior has just been updated. Tropical decor makes you feel like your’e at the beach. Huge flat screen TV. Tile flooring in the living areas and laminate in the bedrooms. Screened lanai overlooks palm tree and mature landscaping. Wireless fast speed internet included. It has everything you need for a short visit or extended stay. Fully equipped kitchen. Washer and Dryer. Beach chairs and towels. One car garage and driveway space.

4.92 out of 5 average rating, 105 reviews

Home in Venice

7 Min to the BEACH 2 King Beds Fenced yard PETS OK

Sandy Flamingo Vacations is offering this spacious and fully renovated home in South Venice, located just south of Sarasota. 2 bedrooms, 2 baths and a bonus room/game room. It is ideal for both work and leisure travel, offering a serene retreat to enjoy activities such as sunny beaches, fishing, boating and exploring. The backyard is fully fenced, featuring a BBQ grill and patio table for outdoor dining. The kitchen is fully stocked, making it suitable for long stays and family cooking.

The exterior of the villa is displayed, featuring a welcoming blue-green door and two large windows framed in white. A small potted plant accents the entrance, while a pathway leads to the door, surrounded by well-maintained grass and greenery.

4.87 out of 5 average rating, 117 reviews

Charming Villa 14 mins away from Siesta Key Beach

This villa close to Siesta Key Beach serves as the perfect escape for those looking to enjoy Sarasota. The property comes fully equipped with amenities such as a BBQ, outdoor umbrella, lounge chairs, beach chairs, pickleball rackets, washer/dryer and carport. Featuring 2 bedrooms, this charming home exudes a warm vibe. You can reach Siesta Key Beach, St. Armands Circle, and Downtown Sarasota in under 15 minutes, making it easy to explore all that Sarasota has to offer during your stay.

The studio apartment features a spacious bed with light-colored linens, complemented by two decorative pillows. A sleek brown sofa is positioned in front, adorned with a soft throw blanket. Natural light enters through the window, enhancing the clean and modern design.

4.81 out of 5 average rating, 206 reviews

Comfortable + Functional Private Studio Apartment

This comfortable, clean, and private studio apartment is the perfect spot to relax- whether you're here on business or you've spent the whole day on the beach! Recently remodeled with a dining table to take your meals, hot water, a comfortable bed, and well equipped kitchenette, you will be lacking nothing here. This apartment is a guest suite attached to the main living area of the home and is completely private, however there is a resident who lives in the main part of the home.

An open living area is presented, featuring a blue couch and a wooden coffee table. A dining table with four chairs sits nearby, complemented by a kitchen with white cabinetry and modern appliances. A Christmas tree adds a seasonal touch, while windows allow natural light.

4.96 out of 5 average rating, 102 reviews

2 BR House 1.6 miles from Siesta Key Beach

Discover the charm of Sarasota in our newly remodeled 2BR/1BA vacation home. Just 1.6 miles from beautiful Siesta Key Beach! Enjoy your morning coffee on a brick patio surrounded by flowers and sunshine. Our comfy beds, blackout curtains, and quiet neighborhood ensure a sweet deep sleep. FIOS wifi and three smart TVs; a fully-equipped kitchen; and a sparkling new bathroom with two sinks, huge mirror, and marble shower offer all the comforts and convenience of home. We welcome you!

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, 106 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 Osprey house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.77 out of 5 average rating, 533 reviews

An inviting beach scene features a sun umbrella providing shade over a wooden lounge chair, set upon soft, sandy shores. The clear blue sky contrasts with the tranquil turquoise waters, creating a peaceful atmosphere near the shoreline.

Home in Siesta Key

Beachfront Getaway in Siesta Key

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, 101 reviews

The Oasis

4.91 out of 5 average rating, 129 reviews

Home in Venice

Spacious 2 Bedroom Home | Near Beach | Heated Pool

The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.

4.89 out of 5 average rating, 167 reviews

5 minutes to private Siesta Key Beach + 2 pools

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, 113 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

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, 128 reviews

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

A private backyard oasis is highlighted by a heated pool and a hot tub, surrounded by lush tropical landscaping. A shaded area with an umbrella and seating for outdoor dining is visible beside the pool, creating a serene environment for relaxation.

4.97 out of 5 average rating, 115 reviews

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

4.92 out of 5 average rating, 382 reviews

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.

Home in Pelican Cove

Beach Retreat•Renovated Pool Patio•Near Siesta Key

Weekly house rentals

4.93 out of 5 average rating, 29 reviews

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.

Home in Arlington Park

Coastal Retreat near Siesta Key Beach and Downtown

A cozy living area is presented with a leather sectional sofa arranged around a round table. Light-colored walls are complemented by a feature wall of rustic wood panels. A flat-screen television is mounted for entertainment, with a view of the dining area and kitchen beyond.

4.9 out of 5 average rating, 29 reviews

Great location! Updated & loaded with all you need

The exterior of a charming turquoise cottage is framed by a fenced yard, featuring a stony pathway and ample outdoor space. Large trees provide a natural backdrop, enhancing the serene environment of this peaceful neighborhood.

4.97 out of 5 average rating, 31 reviews

Costal Breeze Cottage. Pet friendly. King size bed

5 out of 5 average rating, 28 reviews

Sarasota Tropical Place in the Heart of the Gulf!

4.91 out of 5 average rating, 11 reviews

Shoreline Coastal Escape

5 out of 5 average rating, 4 reviews

Modern Lido Key Studio-Steps to Beach & Kayaking

5 out of 5 average rating, 11 reviews

Lux Siesta Key Beach Getway

5 out of 5 average rating, 4 reviews

Beautifully updated home 7 min to Siesta Key Beach

Private house rentals

A spacious living room features light-colored leather sofas arranged around a glass coffee table. A turquoise area rug covers the tiled floor. A large TV is mounted on the wall, and a doorway leads to a dining area with outdoor views.

4.97 out of 5 average rating, 31 reviews

Cottage w/lanai and garage, 4 mi. Siesta Key

A spacious living area is depicted with light-colored tiles. Two sofas, adorned with aqua and gray decorative pillows, face each other. A glass coffee table sits in between, and two lamps provide ambient lighting. A dining area with a circular table is visible in the background.

4.88 out of 5 average rating, 72 reviews

La Villa des Pins

5 out of 5 average rating, 6 reviews

Cottage by the Coast 6 min to Siesta Beach!

5 out of 5 average rating, 18 reviews

The image captures an ocean scene as waves crest against the shoreline, showcasing dynamic white foam. The sky is filled with a gradient of orange and gray hues, signaling sunset, with the sun's rays peeking above the horizon, creating a serene and tranquil atmosphere.

Home in Osprey

5 mins to the beach! Come relax!

5 out of 5 average rating, 4 reviews

Water Access Retreat | Kayaks + Hot Tub

An aerial view showcases the resort-style community featuring a pool area surrounded by comfortable lounge chairs, tennis courts, and lush greenery. Calm ponds reflect the blue sky, enhancing the serene atmosphere of the landscape.

5 out of 5 average rating, 5 reviews

Renovated Sarasota Villa w/ Pool & Private Lanai

An aerial view captures the tranquil surroundings of the property, showcasing nearby waterways and the serene setting of the neighborhood. The proximity to Nokomis Beach is highlighted, with lush greenery and homes present, creating a peaceful coastal atmosphere.

5 out of 5 average rating, 20 reviews

Walking distance to Nokomis Beach!

A welcoming living area is furnished with a blue couch accompanied by bright green and yellow cushions. A wooden coffee table sits centrally, while a small dining table with two chairs is placed nearby. Artworks featuring colorful designs adorn the walls.