Pet-friendly vacation rentals in Osprey

4.92 out of 5 average rating, 38 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

Discover your perfect Florida retreat in this stylish, spacious, and pet-friendly home located in a quiet Palmer Ranch neighborhood. Enjoy an open-concept layout with tall ceilings, a fully stocked modern kitchen, luxury linens, and a fenced-in yard ideal for pets and families. Centrally located near beaches, shops, golf, and top attractions, this elegant getaway offers comfort, convenience, and relaxation. Perfect for extended stays, remote work, and unforgettable family memories all year round

5.0 out of 5 average rating, 28 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, 114 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.

Vacation home in Nokomis

5 * Sarasota 1 min 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!

4.71 out of 5 average rating, 142 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, 98 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.

5.0 out of 5 average rating, 13 reviews

Saltwater Oasis

Welcome to your dream vacation home, where the tranquility of a private saltwater pool meets the convenience of a prime location, just minutes from Nokomis Beach, Legacy Trail and Siesta Key, the USA's #1 Beach. This home offers the perfect blend of comfort, style, and relaxation for your getaway. Our home even features a King sized master bedroom equipped with a sleeper sofa, ensuring young children can stay close to their parents. This is your haven for creating unforgettable memories.

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!

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

Close to the beach and walking distance to 5 restaurants, including one on the water. Our place is less than 2 miles from Nokomis Beach! We have you covered on beach equipment, wagon, chairs, towels and umbrella. The backyard boasts a relaxing, beautiful escape with resort style touches. We have a gas grill to cook your catch, a high powered outdoor fan, and comfy seating in the shade. The house is freshly modernized, open and airy. You will enjoy an outfitted kitchen.

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

Take it easy at this tranquil getaway set on 14 private acres. Close to the beaches, waterfront dining and LegacyTrail, Sarasota county's 20+ bike/walking trail. Nokomis and Casey Key beaches are only 3 miles away, Venice beach 5 miles and historic Venice is 10 minutes away. Close to shopping, grocery stores and boating. Bring your dog. Dog beach and park nearby.High speed internet, large flat screen smart TV and a patio to sit in to enjoy watching the wildlife.

An outdoor deck area is visible, featuring a dining table surrounded by four comfortable chairs and an umbrella. A pair of lounge chairs is positioned nearby. Light blue walls and a decorative anchor add charm to the setting, emphasizing a relaxed atmosphere.

4.91 out of 5 average rating, 45 reviews

Perfect Getaway-Lovely One Bed. House-Near Beaches

Come and Enjoy Beautiful Cottage House. House is located at the one-acre private property in North Venice, Perfect romantic getaway. Experience the laid back, easy culture of Venice in privacy. The house offers a well-stocked kitchen and all the comforts of home. Our spacious cottage captures the feel of Floridian style. Whatever your vacation goals are, they are sure to be met at The Cozy Cottage here in the peaceful, relaxing property of quiet North Venice.

Home in Gulf Gate Estates

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, 132 reviews

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

Spacious 4-bedroom, 2-bath home with a heated private pool, just minutes from the #1 Siesta Key Beach! Located in the Gulf Gate area, you’re only a short drive to the beach, grocery stores, and dining. Enjoy a fully fenced backyard, plenty of parking, and outdoor grill. Inside, you’ll find beach supplies, a fully equipped kitchen, Keurig & drip coffee makers, and TVs in every bedroom—everything you need for a comfortable and convenient stay 🌴☀️

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

The heated saltwater pool is surrounded by a spacious patio area featuring lounge chairs and shaded seating. Lush greenery and fencing provide privacy, while the pool's surface reflects shimmering water patterns under natural light.

4.91 out of 5 average rating, 109 reviews

"Starfish" at The Shore Beach Houses Resort

A covered pool area is visible, featuring a bright blue pool surrounded by spacious pavers. Several lounge chairs are neatly arranged along the pool's edge, with soft illumination highlighting the serene environment and the greenery visible through the screening.

4.98 out of 5 average rating, 102 reviews

Captain's Cottage

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, 108 reviews

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

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

5.0 out of 5 average rating, 5 reviews

Luxury Canal Home | Pool, Spa & Dock Near Beach

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, 73 reviews

Summer sunset. 3 minutes away from beach!

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

5.0 out of 5 average rating, 12 reviews

Coastal Studio Getaway|5 Min to Beach|Pool

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, 112 reviews

Oceanfront home w/sunset views of Sarasota Bay

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, 8 reviews

Beautiful Home on a prestigious 18 holes golf

5.0 out of 5 average rating, 11 reviews

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

The private pool area features a heated pool surrounded by well-maintained landscaping, offering space for relaxation. A colorful beach ball floats on the water's surface. Several loungers and a small dining table are visible, providing options for outdoor enjoyment.

4.97 out of 5 average rating, 29 reviews

Cozy Pool Home Short Drive to Siesta Key Beaches

The outdoor space features a screened-in pool, surrounded by tropical landscaping and a putting green. A barbecue grill is positioned nearby, and several lounge chairs are visible, providing ideal spots for relaxation. The sky is adorned with warm hues of sunset.

4.97 out of 5 average rating, 38 reviews

Intercostal Oasis

Superhost

5.0 out of 5 average rating, 4 reviews

Spacious Home with Private Pool

4.87 out of 5 average rating, 45 reviews

Pets, Plunges & Peace on the Gulf of Mexico

Home in Gulf Gate Estates

4.91 out of 5 average rating, 35 reviews

Sarasota Pool Home| Hot-tub| 2-miles to Siesta

Private, pet-friendly home rentals

5.0 out of 5 average rating, 25 reviews

Guesthouse in Osprey

Private Coastal Getaway - Your Home Away from Home

4.94 out of 5 average rating, 17 reviews

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

5.0 out of 5 average rating, 41 reviews

Sarasota Tropical Place in the Heart of the Gulf!

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, 62 reviews

Viva life Residence

A two-story house is framed by lush greenery and palm trees. A paved driveway leads to the entrance, which is elevated on stilts. A black mailbox stands on the front lawn, providing a welcoming touch to the exterior.

4.89 out of 5 average rating, 9 reviews

Serenity on Stilts

Home in Gulf Gate Estates

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, 72 reviews

Coconut Cottage 5 min drive to Siesta Key

5.0 out of 5 average rating, 44 reviews

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.

Home in South Venice

Venice retreat-steps to Shamrock Park/Legacy Trail