House holiday rentals in Osprey

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.

4.98 out of 5 average rating, 53 reviews

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!

5 out of 5 average rating, 6 reviews

Mango Mansion - Beach Escape 3 Min. From Beach

Escape to this spacious 2BR/2BA beach house in Nokomis, FL! Perfect for families & groups, it sleeps up to 10 guests. One side of duplex. Avo. tree, 2 mango trees, tangerine tree and key lime tree on property. Enjoy the open great room for gathering, cook in the fully equipped kitchen , and relax on the screened lanai . Just 3 minutes from Nokomis Beach & Casey Key, this home has everything you need for a fun, comfortable stay — plenty of space, modern amenities, and a welcoming coastal vibes.

A single-story home with a gray exterior features a bright yellow front door. The property showcases a well-maintained lawn and a spacious driveway. Outdoor seating is arranged on a patio area, surrounded by greenery and trees, creating an inviting space for relaxation.

5 out of 5 average rating, 26 reviews

Sand Dollar Retreat

Escape to our relaxing 2-bedroom home in Osprey, Florida, just minutes from the stunning beaches of the Gulf of Mexico, pristine golf courses and MLB spring training. This peaceful retreat sleeps up to 7 adults and offers a perfect blend of comfort & convenience. The master bedroom features a queen bed and the second bedroom has a bunkbed sleep system with a queen mattress on bottom and twin mattress elevated above. There is also an office with a daybed & trundle for additional sleeping space.

An outdoor dining area features a wooden table with two matching chairs positioned on a patterned rug. A decorative wall with colorful fish accents and a window reflects natural light. A door leads to the interior space, framed by lush greenery.

4.96 out of 5 average rating, 28 reviews

The Nautilus Casita

A cozy spot to unwind the day after enjoyingTiki Bars, beaches and all Sarasota has to offer. We are 6 minutes from the Gulf and its white sandy beaches. Enjoy fishing the Jetty, boating the ICW, biking Legacy trail and enjoying sunsets at the Tiki bars with a famous grouper sandwich. So many activities to choose from in this town nestled next to the nation's #1 beach destination, Siesta key. All pets MUST be on a vet approved flea medication & proof sent prior to check in. No exceptions.

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, 25 reviews

Updated house close to the Beach

Just 5 minutes from Nokomis beach! Renovated 2 bedroom, 1 bath house. It has full kitchen with granite countertop and island. 1 bedroom with queen bed and second bedroom with 2 twin beds. Big backyard partially fenced. It is close to shopping, restaurants and I-75, perfectly located between Sarasota and Venice. It is fully equipped with all amenities needed for your stay: beach chairs and umbrellas. Washer and dryer, dishwasher, WI-FI, LED TVs. Bring your family to enjoy this peaceful place.

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, 117 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.

The exterior of a duplex is displayed, featuring a light-colored stone facade and a red-tiled roof. A spacious driveway leads to a two-car garage, surrounded by well-maintained landscaping with palm trees and shrubbery. A clear blue sky adds brightness to the scene.

5 out of 5 average rating, 12 reviews

Comfortable Secluded Villa in Sarasota

Relax at this peaceful duplex on a private cul-de-sac location in Village des Pins. It's a short walk to a large resort-style community pool, pickleball and tennis courts, a clubhouse with outdoor grilling and seating. The unit is 1,353 sq ft and has 3 new flat-screen TVs. Spacious living room overlooks the private rear view with a tiled, screened lanai. Master has king bed with huge walk-in closet. Split bedroom plan for added privacy. The world-famous Siesta Key Beach is 15 minute drive!

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, 208 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.

Superhost

A modern living space is displayed, featuring a large gray sectional sofa and a circular wooden coffee table. The sleek kitchen with dark cabinetry is in view, complemented by pendant lighting and a spacious countertop. Natural light enters through the windows, enhancing the contemporary design.

4.89 out of 5 average rating, 92 reviews

Private house with loft

Have fun with the whole family at this brand new, modern private free standing guest house. Full bedroom with king size bed, with a finished loft including a queen bed. There’s also a queen pull out sofa in the living area. Enjoy your privately fenced backyard with a hot tub and putting green. Centrally located between Siesta Key beach and Nokomis beach. Hot tub is available upon request in off season months, April-October. There will be an additional $30 fee in off season months.

5 out of 5 average rating, 11 reviews

Lux Siesta Key Beach Getway

February Special DISCOUNT send us a message now! Beach home under 11 minutes to Siesta Key beach & attractions : 20 minutes to the airport 15 minutes to UTC Hammock Fire pit Foosball Backyard patio seating Grill Cozy Decor Comfy beds Fully stocked kitchen Fully stocked bathrooms Minutes to shops & restaurants Quite and safe location Escape to this beautiful home in quiet South Sarasota The perfect blend of comfort, location, and charm for your beach tea

Popular amenities for Osprey house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a 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, 142 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

The modern kitchen features a large island with a marble countertop, topped with an arrangement of fresh fruits and drinks. A light fixture adds a soft glow above the island, while a cozy seating area with a dark sofa and brick wall can be seen in the background.

4.87 out of 5 average rating, 112 reviews

Sarasota Getaway “Have some fun under the sun.”

4.78 out of 5 average rating, 534 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.

4.98 out of 5 average rating, 103 reviews

The Oasis

4.92 out of 5 average rating, 130 reviews

Home in Venice

Spacious 2 Bedroom Home | Near Beach | Heated Pool

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 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, 169 reviews

5 minutes to private Siesta Key Beach + 2 pools

A relaxing outdoor space features a sparkling swimming pool surrounded by lounge chairs with red and white stripes. Tall palm trees stand nearby, adding a tropical touch, while serene water views and lush greenery are visible in the background.

4.91 out of 5 average rating, 78 reviews

Oceanfront Home with Heated Pool in Fishers Haven

Weekly house rentals

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.

4.98 out of 5 average rating, 50 reviews

Sarasota vacation Home!

5 out of 5 average rating, 12 reviews

Nokomis Waterfront Unit Walk to the Beach & Dining

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

4.93 out of 5 average rating, 30 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 modern kitchen is highlighted by a central island with a dark countertop and multiple drawers. Sleek white cabinets complement stainless steel appliances, while a coffee maker and kettle are positioned on the counter. A potted orchid adds a touch of color to the space.

4.99 out of 5 average rating, 78 reviews

Luxury Pet friendly home, 2.7miles to Siesta Key!

4.92 out of 5 average rating, 12 reviews

Shoreline Coastal Escape

A wooden boardwalk leads through lush greenery toward a sandy beach, where colorful umbrellas are scattered across the shore. The clear blue sky meets the tranquil ocean, and beachgoers can be seen enjoying the space.

4.89 out of 5 average rating, 46 reviews

Beach house

The living area features a spacious sectional couch with a contemporary design, comfortably accommodating multiple guests. A large television is mounted on the wall, displaying a serene sunset scene. Natural light filters through the windows, highlighting the sleek decor and open layout that connects to the kitchen.

4.9 out of 5 average rating, 21 reviews

Pet-Friendly Modern Retreat Near Siesta Key

Private house rentals

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, 82 reviews

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

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

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.

5 out of 5 average rating, 18 reviews

5 mins to the beach! Come relax!

5 out of 5 average rating, 45 reviews

Home in Englewood

"Lost Loon" Oceanfront Cottage by Roxy Rentals

4.95 out of 5 average rating, 38 reviews

A dining area features a long, light wood table set with woven placemats. The walls are adorned with a vibrant palm leaf wallpaper, complementing the natural light that streams in through multiple windows. A modern light fixture hangs above the table, adding a contemporary touch.

Home in Laurel Park

Julia Place-walk downtown from old Florida glam!

4.85 out of 5 average rating, 99 reviews

Lovely Studio |6 miles to Siesta Key Paradise

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.

4.97 out of 5 average rating, 58 reviews

Family-Friendly Retreat Near Siesta Key+Beach Gear

A charming house is set within a spacious yard, featuring lush green grass and palm trees. A driveway leads to a light-colored exterior, with the front entrance framed by tropical plants. A clear blue sky adds to the inviting atmosphere of the property.