Pet-friendly holiday rentals in Osprey

Bungalow in Gulf Gate Estates

4.84 out of 5 average rating, 117 reviews

Beach Remedy Retreat near Siesta Key Beach

Unwind & Refresh! Our perfect 3/2 getaway is fully remodeled and our cozy retreat rests in the most ideal location for everything Sarasota has to offer! Just 2 mi. to Siesta Key Beach! Beach towels, chairs & toys provided. Grocery, restaurants and unique shops within 1.5 mi. Indulge in watching gorgeous sunsets, walks on the beach, shop/dine in the many cafes in our community. Extras for your use-hammock, outdoor grill, board games, books, large screened in patio. Family neighborhood. Enjoy!

4.89 out of 5 average rating, 107 reviews

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

Welcome to The Salty Unicorn, your cheerful Sarasota escape just five miles from Siesta Key Beach. This fully renovated 3-bedroom home is designed for relaxation and fun, with a bright open layout, stylish coastal décor, and plenty of space to gather with family or friends. Start your mornings with coffee by the pool, spend sunny afternoons swimming or lounging in the spacious backyard, and end the day with dinner in the screened lanai. Whether you’re here for beach days, family time, or a peace

5.0 out of 5 average rating, 30 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!

Relax with the family at this peaceful place to stay. Home located in a unique family friendly neighborhood on the inter-coastal. Enjoy family games, watching the sunset from the lanai and using the enclosed outdoor shower after a day at the white sandy beach! Take out our 2 kayaks on the intercoastal and explore the area. Nokomis beach 5 minutes away and Siesta key 7 miles. So many cute restaurants nearby on the water. Stroll through the neighborhood and see all of the beautiful homes and boats

4.87 out of 5 average rating, 116 reviews

A modern kitchen with stainless steel appliances includes a refrigerator and stove. A dining table with two chairs is positioned nearby, while a comfortable sofa is viewed in the open living area, adjacent to a cozy sleeping space with light-colored bedding.

Holiday home in Nokomis

Sept Sale! #1 Sara BEACH Villa/King /Pets/yard OK!

Our unique villas sit just 1/2 mile from one of Florida’s most pristine beaches. Many local restaurants and shops are easily accessible. The villas also have an attached yard/field perfect for pets, 40 lb max total weight . The local beach is considered one of Florida’s finest with only one access point for over 7 miles of private beach! We have been super hosts for years and love creating great memories Please read our reviews! Two adults, two kids maximum capacity...:) Chris and Michelle!

5.0 out of 5 average rating, 42 reviews

Sarasota Tropical Place in the Heart of the Gulf!

Forget your worries in this spacious and serene space and enjoy all the magic Sarasota has to offer. This charming home is a 3 bedroom 2 bathroom with an open light living room. Kitchen fully stocked will meet all your cooking needs. Other amenities include TV, WIFI, and gas BBQ grill with patio Chaise Lounge Chairs. A fenced in patio with lush palms.This beautiful home is the perfect getaway for friends and families that is conveniently located in the heart of the Gulfs most beautiful beaches.

4.71 out of 5 average rating, 143 reviews

The front exterior of the house is featured, showcasing a well-maintained garden with shrubs and small plants. A concrete walkway leads to the entrance, with a single chair positioned beside it. The garage door and house number are clearly visible.

Flat in Osprey

Great one bedroom apartment near beaches in Osprey

Our rental features a one bedroom with an attached living room and private bathroom. The bedroom offers a queen bed, walk in closet. The living room has a large couch and tv. Full equipped kitchen with a laundry room. The apartment has its own private front door entrance and driveway parking. Friendly for dogs to safety run outside (gated). The house is located 12 min away from Siesta Beach (ranked #1 in Fl) and 10 min away from Nokomis Beach. We are placed between Venice and Sarasota. WiFi

A serene view of the canal is presented, featuring lush greenery along the water's edge. A wooden dock extends into the calm waters, with a single folding chair positioned nearby. Colorful flowers add vibrancy to the scene, creating a peaceful outdoor atmosphere.

4.93 out of 5 average rating, 107 reviews

Welcome to Paradise Palms! Canal home/Pet friendly

Canal front home in Nokomis, right next to Legacy Trail. Bicycles and Kayaks available to enjoy a trip to the beaches and local islands, please sign waivers before using and send to hosts. Fish right off your dock and enjoy covered Lanai with outdoor fireplace. Nokomis beach (2 miles), Venice beach (2.5 miles), Jetti beach (3 miles). Close to restaurants and historical Venice shopping. This home can sleep up to 8 people. Pets are welcome (125$ pet fee) Please be courteous noise late night.

4.87 out of 5 average rating, 186 reviews

A modern studio layout features a queen bed with a blue floral bedspread, complemented by a comfortable futon and decorative pillows. A small dining table with two chairs is positioned near the seating area, while large blue curtains frame the window, allowing natural light to enter.

Flat in Sarasota

Chic & Cozy Getaway • Near Siesta Key Beach

Renovated modern studio in a duplex home with private entrance, full kitchen, bathroom, laundry, and parking. Nestled in a quiet, safe neighborhood just minutes from Lido, Turtle, Nokomis beaches, and Siesta Key—#1 beach in America with soft, white sand. Walk to restaurants, Starbucks, Total Wine, Costco, Target, CVS, Bay Village Assisted Living, Selby Aquatic Center & Vamo Bay Park. Short drive to downtown Sarasota, Venice & scenic bike trails. Ideal for beach getaways or extended stays!

A single-story house is set within a lush green landscape, featuring well-maintained shrubs and palm trees. The façade includes large arched windows and a spacious driveway nearby, with bicycles visible against the side of the house. A clean lawn invites outdoor activities.

4.93 out of 5 average rating, 137 reviews

Sunny Oasis/Beautiful House/Near Beach/Heated Pool

Beautiful House with 3 bedrooms, heated pool, mini golf and two-car garage. Great location. five-minute drive to the beach. near shopping plazas, restaurants, and the famous Legacy Trail perfect for biking, running, and more. Situated at a dead-end in a peaceful community. Lots of outdoor space around the house with beautiful palm trees and a large patio. bicycles, board games, cornhole, a gas grill, and more at your disposal. Lots of places to visit in the Sarasota and Venice area.

A modern kitchen features dark wood cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and dishwasher, are included. A doorway leads to a bright living area where natural light filters through a window, illuminating a cozy seating arrangement.

4.96 out of 5 average rating, 277 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Walking distance to a Publix grocery store and 5 good restaurants. ⅕1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. New tile and wood floors throughout. Quite neighborhood for walking .

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.

4.97 out of 5 average rating, 141 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!

4.96 out of 5 average rating, 52 reviews

The property is surrounded by lush greenery, featuring a spacious driveway leading to a single-story home. Tall palm trees and various plants are visible in the yard, creating a tropical ambiance. The structure is situated in a serene neighborhood, showcasing nature's beauty.

Home in Osprey

Creekside Paradise I

The 1970 sqft living space hosts 3 bedrooms, 2 bathrooms, an open living room with attached ‘library’, a dining area, as well as a fully equipped kitchen. From the caged pool area you have a view of the North Creek and our Boat Dock. The pool can be electrically heated and measures 32.80ft in length/13.12ft in width. You enter Creekside Paradise I thru the attached 2 car garage, where you can find the beach equipment (chairs, umbrella, cooler).

Popular amenities for Osprey pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 134 reviews

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

4.94 out of 5 average rating, 101 reviews

A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.

Home in South Sarasota

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Colorful swinging chairs are suspended from a wooden frame in a lush backyard. A small round table rests on the deck beneath a cloudy sky, surrounded by greenery and a fenced perimeter.

4.97 out of 5 average rating, 130 reviews

Cute Little Getaway

A spacious pool area is surrounded by a screen enclosure, offering a clear view of the turquoise saltwater pool. The patio features a few lounge chairs and a table, with a grassy backyard visible through the enclosure, enhanced by the natural light streaming in.

5.0 out of 5 average rating, 14 reviews

Nokomis Serenity Oasis

A modern kitchen is highlighted by navy blue cabinetry and white quartz countertops. Stainless steel appliances, including a refrigerator and microwave, are visible. Pendant lights hang above an island with seating for several. The space is brightened by recessed lighting and a window offering natural light.

4.97 out of 5 average rating, 36 reviews

La Niña 5 minutes to Nokomis Beach Fenced In Yard

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, 71 reviews

Family-Friendly Retreat Near Siesta Key+Beach Gear

4.83 out of 5 average rating, 40 reviews

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.

Home in Osprey

Pet-Friendly Modern Retreat Near 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.

4.88 out of 5 average rating, 64 reviews

14 acre home peaceful, private, 5 minutes to beach

Pet-friendly home rentals with a pool

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, 114 reviews

Oceanfront home w/sunset views of Sarasota Bay

4.94 out of 5 average rating, 179 reviews

Home in Sarasota Springs

Lake Front House with a Pool

A heated pool is surrounded by lush tropical plants and palm trees, offering a relaxing atmosphere. Adjacent to the pool, a tiki bar provides seating for several guests, complemented by a flat surface for refreshments. The area is enhanced by a well-maintained garden visible beyond the pool.

4.95 out of 5 average rating, 111 reviews

Tiki Oasis 3bed on .6 acre paradise 5 min to Beach

A screened-in heated pool area is featured, reflecting clear blue skies and fluffy clouds. Comfortable outdoor seating is positioned beside the pool, complementing the serene atmosphere. The pool area is framed by a spacious deck, enhancing the overall inviting design.

4.85 out of 5 average rating, 129 reviews

Perfect Getaway 3bd/2bth Private Heated Pool

A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.

4.8 out of 5 average rating, 185 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

A screened-in pool area is showcased, featuring a clear water swimming pool tiled along the edges. Sunlight reflects off the surface, while lounge chairs are visible in the background, surrounded by lush greenery.

5.0 out of 5 average rating, 9 reviews

Beautiful Home on a prestigious 18 holes golf

5.0 out of 5 average rating, 17 reviews

Cool home w/heated pool near beach

4.87 out of 5 average rating, 46 reviews

Pets, Plunges & Peace on the Gulf of Mexico

Private, pet-friendly home rentals

The front exterior of a single-story home is displayed, featuring a light-colored facade and a welcoming entryway. Surrounding greenery and a white fence frame the property, with a gravel driveway leading up to the entrance. Soft clouds are visible in the sky above.

4.97 out of 5 average rating, 66 reviews

Viva life Residence

A charming house is situated on a cul-de-sac, featuring a well-maintained exterior and a single-car garage. Lush greenery and palm trees surround the home, contributing to a serene setting. The driveway is spacious, leading to the entryway, which can be seen through the open front porch.

4.87 out of 5 average rating, 38 reviews

Nirvana In Nokomis

4.94 out of 5 average rating, 18 reviews

3/2 near Beaches! Pet Friendly•Patio• Fox Lea Farm

4.91 out of 5 average rating, 55 reviews

Beach house

5.0 out of 5 average rating, 20 reviews

Nokomis Beach | Canal Front Unit | Boat Friendly

The exterior of a beach cottage features peach-colored walls and a bright teal front door. Surrounding greenery includes palm trees and other tropical plants, contributing to a relaxed atmosphere. A concrete pathway leads to the entrance, while a small seating area is visible on the porch.

5.0 out of 5 average rating, 6 reviews

Florida Gem close to Nokomis Beach & Venice DT

A charming beach villa is set against a sunset sky, framed by lush greenery and vibrant landscaping. Soft lighting adorns the exterior, highlighting the welcoming entrance. A gravel driveway leads to the home, surrounded by decorative plants and stones.

4.9 out of 5 average rating, 73 reviews

Coconut Cottage 5 min drive to Siesta Key