Pet-friendly vacation 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!

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

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.

Apartment 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

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!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

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.

Apartment 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 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

Welcome to your private Oasis, with a large private backyard filled with fruit trees and saltwater pool that meets the convenience of a prime location, just minutes from Nokomis Beach, and Legacy Trail. Casperson Beach, shark tooth hunters dream, is a short drive over to Venice Island to enjoy Venice Beach and charming local shops and dining or take a short ride north to Siesta Key Beach, USA's #1 Beach, and Siesta Village offering direct beach access and charming local shops and dining.

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.

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, 121 reviews

A sandy pathway leads to the beach, framed by lush greenery and tall grasses. The gentle waves of the ocean are visible in the distance, with a clear blue sky overhead. Sunlight casts a warm glow on the pathway, inviting relaxation.

Condo in Venice

Short walk to beach 4, King bed, Dog Friendly

Location Location Location! A few steps to beach, and short walk or bike ride down the tree lined boulevard takes you to Historic Downtown Venice where you'll find, Restaurants, Cafes, and Boutiques. Experience island life from this 1 BR, 1st floor condo, walk to everything. Pack your bathing suit, and flip flops, with all the comforts of home, beach towels, umbrella, and chairs, provided, that's all you'll need here! Sofa bed also available.

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).

4.98 out of 5 average rating, 188 reviews

Cottage in Nokomis

Staycation Sanctuary

Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!

Popular amenities for Osprey pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.89 out of 5 average rating, 107 reviews

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

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

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, 140 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

A welcoming living area displays a neutral color palette, featuring a comfortable gray sofa and a light wood coffee table. A large television is mounted on a wall adorned with ocean-themed art. Soft natural light filters in, creating a serene atmosphere.

4.76 out of 5 average rating, 134 reviews

Cozy Beach Cottage

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

4.93 out of 5 average rating, 156 reviews

A sandy beach stretches toward a wooden pier that extends into the ocean. The sun sets on the horizon, casting warm golden hues across the sky and reflecting on the gentle waves.

Home in Venice

A Dream Come True

The spacious kitchen features a large island with seating for six, complemented by modern white cabinetry and stainless steel appliances. Natural light floods the area through sliding glass doors that lead to the outdoor space, enhancing the open feel of the home.

4.97 out of 5 average rating, 59 reviews

Spacious Gulf Escape 7 min to Nokomis Beach Pets

4.83 out of 5 average rating, 41 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

Pet-friendly home rentals with a pool

A spacious backyard features a heated private pool surrounded by a paved area. Lounge chairs are positioned around the pool, with umbrellas providing shade. Lush greenery and a fence frame the yard, creating a serene outdoor setting, ideal for relaxation.

4.8 out of 5 average rating, 137 reviews

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

4.94 out of 5 average rating, 179 reviews

Home in Sarasota Springs

Lake Front House with a 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, 187 reviews

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

Apartment in Gulf Gate Estates

A light-filled living area features a soft blue sofa adorned with decorative pillows. Large sliding glass doors open to a private screened lanai, enhancing the connection to the outdoors. A simple coffee table is centered on a cozy area rug, with a TV placed against the opposite wall.

4.86 out of 5 average rating, 199 reviews

Little Gem 2nd-Floor Condo w/ Heated Pool | 1BR

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 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

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.

4.97 out of 5 average rating, 39 reviews

The Nautilus Casita

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 screened-in patio is featured with comfortable seating made of woven material. A low table sits in the center with decorative items. The backdrop includes soft purple hues from the sunset and surrounded by tropical plants, offering a serene outdoor setting.

4.96 out of 5 average rating, 75 reviews

Summer sunset. 3 minutes away from beach!

4.88 out of 5 average rating, 75 reviews

Cozy and private in Sarasota

5.0 out of 5 average rating, 21 reviews

Nokomis Beach | Canal Front Unit | Boat Friendly

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

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.