House holiday 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 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

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 well-lit dining area features a modern table with four chairs, complemented by a floral artwork on the wall. Natural light enters through French doors, enhancing the bright and open atmosphere. A stainless steel refrigerator is visible, maintaining a clean and functional kitchen space.

4.9 out of 5 average rating, 108 reviews

Tropical Paradise minutes to #1 Siesta Key Beach

Location! Just minute to the #1 Beach in USA , Siesta restaurant and shopping. This cozy 2 bedroom/1 bath home feels very modern, comfortable and very functional. Tropical landscaping .Fully equipped kitchen. Beautiful private fenced backyard with Yoga platform. Beach chairs available. Perfect for a budget oriented traveler looking for immaculate home and convenient location close to Hwy 41 Siesta Beach and shopping and walking distance to restaurants. Primary guest must be 25 years of age.

The outdoor space is enclosed by a screened lanai, showcasing a heated saltwater pool and a dining area with a large table that seats eight. Lounge chairs and a BBQ grill are positioned near the pool, surrounded by tropical landscaping and a clear blue sky.

4.96 out of 5 average rating, 101 reviews

3 bedroom Heated salt water pool close to Siesta

Your family will be close to everything when you stay at this centrally-located place. 15 minutes to Siesta Beach, 10 minutes to UTC mall, 15minutes to downtown, 20 minutes to SRQ airport. This home is fully remodeled, fully furnished, sleeps 8. We have 1 king size bed in the master, second bedroom is queen bed, 3rd bedroom is 1 full and 1 twin beds. This is open plan home with a big family room, 60" TV above electric fireplace, formal dining room seats 6 with the bar seats 4. Master has 55"TV

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, 114 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!

4.92 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

Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

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!

4.92 out of 5 average rating, 269 reviews

A welcoming entryway features a bright door with a small window and a decorative hanging piece. Light-colored walls surround a cozy seating area with a modern sofa. A simple side table holds a lamp, and framed artwork decorates the walls, complemented by indoor plants.

Home in Gillespie Park

*Downtown home 10min. drive to beach; walk DT*

In the heart of Gillespie Park, this bright & spacious home is a 10 min. drive to Lido Beaches and within walking distance to downtown shops, grocery, farmer's market, opera house, restaurants, bars, live music, tennis, parks, antique shops and performing arts. Old Florida bungalow on the outside, inside, it's updated with new appliances and bathrooms. A banyan tree offers private, shady repose on the back deck w/grill and dining area. Message me for room availability.

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 house rentals in Osprey

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 private hot tub is shown within a screened enclosure, featuring clear blue water. Two inflatable rings are floating on the surface. Lush greenery can be seen in the background, providing a natural setting for relaxation.

4.98 out of 5 average rating, 104 reviews

Location! Siesta 1 mile away. Home with HOT SPA.

4.91 out of 5 average rating, 129 reviews

Home in Venice

Spacious 2 Bedroom Home | Near Beach | Heated Pool

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, 112 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

A secluded backyard features a heated pool surrounded by lush greenery and flowering plants. Tropical palm trees and colorful potted plants enhance the tranquil atmosphere, while the tiled pool edge adds a touch of contemporary design.

4.84 out of 5 average rating, 291 reviews

Private Siesta Beach House Oasis with Heated Pool.

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!

A serene outdoor seating area features several lounge chairs with cushions, positioned on a brick patio overlooking tranquil water. The setting is complemented by a soft sunset in the background, with lush greenery visible across the bay.

4.89 out of 5 average rating, 105 reviews

Oceanfront home w/sunset views of Sarasota Bay

4.93 out of 5 average rating, 103 reviews

A close-up view of delicate white flowers is presented in the foreground, while a serene heated pool is visible in the background. Sunlight reflects off the clear water, with a hint of colorful pool floats resting on the surface in a well-maintained outdoor space.

Home in Venice

Modern 3-Bedroom Home with a New Pool

Weekly house rentals

5 out of 5 average rating, 17 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!

A screened-in porch is featured with a round glass-top table surrounded by four wicker chairs. Decorative string lights are hung above, creating a cozy environment. Lush greenery is visible through the surrounding windows, enhancing the outdoor feel while maintaining indoor comfort.

4.96 out of 5 average rating, 57 reviews

Family-Friendly Retreat Near Siesta Key+Beach Gear

4.86 out of 5 average rating, 64 reviews

The exterior features a well-maintained house surrounded by grassy lawns and tropical landscaping. Palm trees and shrubs provide natural shade, while a driveway leads to a single-car garage. The exterior is brightened by soft evening light, creating a welcoming ambiance.

Home in Venice

Venice Gardens, 2-Br Pet Friendly Home - Indra

5 out of 5 average rating, 4 reviews

Modern Lido Key Studio-Steps to Beach & Kayaking!

A one-story house is shown with a carport on the left side. The front yard features low shrubs and tall palm-like plants. Large windows are visible, allowing natural light to enter. The house is set against a background of trees and a clear blue sky.

5 out of 5 average rating, 23 reviews

Updated house close to the 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.

4.94 out of 5 average rating, 32 reviews

Cottage Chic Near Siesta Key Beach!

5 out of 5 average rating, 4 reviews

Beautifully updated home 7 min to Siesta Key Beach

A charming blue house is presented with a gabled roof and dormer windows. Lush greenery and colorful flowers surround the entrance, which features a white door and inviting walkway. The bright sky with scattered clouds complements the vibrant exterior and landscaped yard.

5 out of 5 average rating, 23 reviews

Casa Playa Sleeps 6

Private house rentals

The exterior of the home is highlighted by a manicured lawn and palm trees, framed by a driveway leading to a wooden garage door. A clean, modern design features a light-colored facade under a silver metal roof, set against a clear blue sky.

4.92 out of 5 average rating, 62 reviews

Perfect Getaway Home - 12/min from siesta w/HotTub

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

The exterior of a single-story house is framed by lush greenery and palm trees. A wide driveway leads to a garage with a white door. The entrance is adorned with potted plants and shrubs, set against a backdrop of trees that provide shaded tranquility.

4.86 out of 5 average rating, 56 reviews

14 acre home peaceful, private, 5 minutes to beach

4.99 out of 5 average rating, 94 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

Private Standalone Home - Walk to Siesta Key Beach

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

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 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

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.