House vacation rentals in Osprey

4.98 out of 5 average rating, 50 reviews

A spacious living area features a light-colored sectional sofa and a round coffee table in the center. Natural light pours in through large windows, illuminating the room's wood accents and open layout. A dining area with a wooden table and chairs is visible in the background.

Home in Osprey

Charming Florida Cottage - Kayaks Included

Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida. Enjoy exploring Historic Spanish Point, kayaking to a secluded beach, walking to Historic Bay Preserve, watching the sunset over the Bay, fishing at Osprey Fishing Pier, walking to dinner all from your well appointed and peaceful oasis. There is no better place to experience true Florida living!

4.73 out of 5 average rating, 346 reviews

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.

Home in Nokomis

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, 206 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 charming cottage is nestled among lush greenery, surrounded by tall trees and palms. A gravel pathway curves gently around the property, enhancing the serene outdoor setting. Sunlight filters through the foliage, creating dappled light across the landscape.

4.96 out of 5 average rating, 170 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

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!

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.

4.93 out of 5 average rating, 375 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

☀Coastal Gem☀Heated pool & amazing location!☀

- Located in a quiet Sarasota neighborhood minutes from shopping, restaurants, & Siesta Key, this amenity packed home is perfect for families and beach enthusiasts! - Enjoy the pool and patio (renovated in July 2025) and comfy outdoor furniture in your fenced in backyard where you can bask in the sun. - Beautifully designed coastal interior w/ new appliances, Smart TVs, and fast WiFi. - Your on-site Superhost is available if needed to assist with making your stay enjoyable and worry free.

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, 199 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.

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!

An outdoor seating area features four woven lounge chairs arranged around a small table, set on a stone patio. Lush greenery, including tall plants, surrounds the space, providing a sense of privacy. Natural light filters through the windows of the adjacent building.

4.8 out of 5 average rating, 128 reviews

PERFECT FLORIDA GETAWAY !

Only 5min from Venice historic downtown and 10min from Venice beach ! Very well located, our vacation rental home offers everything you need to enjoy your stay. The apartment is a 1bedroom/1bathroom for 2 people. Totally separated from the main house. Restaurants and shops in beautiful historic Venice downtown. Close to many beaches and the Legacy Trail. About 7 miles from Siesta Key, America's #1 beach !

4.95 out of 5 average rating, 100 reviews

Near Beach•Air Hockey• Ping-Pong•Bikes•Beach Gear

Welcome to Vistalodgings Casa Del Mar. 🌴🌊☀️ Modern house in Venice, 8 minutes drive to the beach, close to restaurants, and shops. 5 minutes to Publix, 4 minutes to Walmart. Situated in a serene and relaxing neighborhood with completely fences backyard. Bicycles, beach stuff, outdoor gas grill, and beach towels are available. Plenty of nearby beaches to choose from.

Popular amenities for Osprey house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A tranquil heated swimming pool is enclosed by a screened patio, with clear blue water reflecting the sky. Surrounding palm trees add a touch of tropical greenery, while a shaded seating area is visible in the background, creating an inviting outdoor space for relaxation.

4.96 out of 5 average rating, 112 reviews

Venice Getaway 3 bedrooms, private heated 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!

4.97 out of 5 average rating, 256 reviews

Your private retreat near Siesta Key Beach.

A spacious and private swimming pool area is enclosed by a screened lanai, providing a sheltered space. Several lounge chairs are positioned around the pool, which features clear water and steps leading in. A door leads to the interior of the house, enhancing accessibility.

4.89 out of 5 average rating, 205 reviews

Perfect vacation home 3 miles from beach.

4.91 out of 5 average rating, 125 reviews

Spacious 2 Bedroom Home | Near Beach | Heated 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, 126 reviews

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

5 out of 5 average rating, 117 reviews

Home in Bellevue Terrace

Living The Dream - Heated Pool + Mini Golf +Swings

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, 102 reviews

Oceanfront home w/sunset views of Sarasota Bay

Weekly house rentals

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

Superhost

Home in Osprey

5 out of 5 average rating, 3 reviews

The Pool house retreat

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

4.97 out of 5 average rating, 59 reviews

The living area features a floral-patterned couch and loveseat positioned around a wooden coffee table. Natural light enters through a window adorned with sheer drapes. A small dining space is visible in the background, furnished with a table and four chairs, along with decorative wall art.

Home in Bradenton

Hello Sunshine! 1 mile from IMG

A spacious bedroom is illuminated by natural light from sliding glass doors. The area features a large bed with blue accents, a comfortable armchair, and a desk. A muted rug complements the wooden flooring, while plants and decor add a touch of greenery.

4.97 out of 5 average rating, 31 reviews

Resort-Style Vacation Villa

A serene beach scene displays soft sand meeting gentle waves under a bright sky. The water showcases a gradient of blue hues, while fluffy white clouds add to the tranquil atmosphere. Footprints can be seen leading towards the shoreline, inviting exploration.

4.95 out of 5 average rating, 40 reviews

Dolphin Cottage

5 out of 5 average rating, 11 reviews

Luxury Siesta Key |Beach Home

Private house rentals

4.98 out of 5 average rating, 50 reviews

The exterior of a single-story coastal home is presented, featuring a light-colored façade with stone accents. A curved driveway leads to a garage, and lush landscaping complements the structure, providing a welcoming atmosphere. Blue accents on the front door enhance the inviting entryway.

Home in Osprey

Sarasota vacation Home!

A spacious living room is presented with neutral-toned sofas adorned with colorful cushions. A coffee table with decorative items is centered between the seating, while light enters through large windows framed by soft blue curtains. A decorative plant adds a touch of greenery.

5 out of 5 average rating, 33 reviews

Great Rates! Sunny Sarasota Villa! W/ 2 bicycles!

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, 29 reviews

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

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!

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, 9 reviews

Pool house with outdoor shower, 10 minutes from SK

A charming single-family home features a freshly painted exterior with a light blue front door. Lush greenery, including palm trees and flower beds, enhances the inviting curb appeal. A driveway leads to an attached garage, and a neatly maintained lawn stretches across the property.

4.91 out of 5 average rating, 68 reviews

Palmetto Cottage Retreat

A vibrant beach scene displays colorful beach chairs and mats arranged on the sand. An orange boogie board leans against one chair, while a variety of patterned beach towels add to the inviting setup. The backdrop includes distant palm trees and a clear blue sky.