Pet-friendly vacation rentals in Osprey

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Osprey

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Sarasota

4.88 out of 5 average rating, 137 reviews

Pets friendly modern studio 5 mi to Siesta Key

Renovated Studio/1 full bath apartment in a duplex house with separate entrance in a quiet and secure neighborhood. Located in a West of "The Trail" in Southern Central Sarasota. Ideally close to Siesta Key, Turtle, Osprey and Nokomis beaches. Bike Routes throughout and short drive to downtown Sarasota, Osprey, Venice and wonderful amenities of Sarasota Lifestyle. Walking distance to restaurants, Selby aquatic center, Vamo Sarasota Bay Park, Westfield Mall, Total Wine, Costco, Target and CVS.

Aug 9 – 16

R2,049 ZAR per night

Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 128 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.

Sep 22 – 29

R2,769 ZAR per night

Guest favorite

Guest suite in Sarasota

4.98 out of 5 average rating, 192 reviews

The Sapphire Suite 1Bed/1Bath

Beautifully elegant suite with a relaxing touch. A pleasant mix of Hispanic and Modern decor in a newly renovated living area complete with all necessities such as wifi, an outdoor patio and your own free parking. The suite is located MINUTES away from all of Sarasota's famous hotspots! It is down the street from Jungle Gardens. A 10minute walk to The Ringling Museum. 10minute drive to Downtown, 15 minute drive to both Siesta Key and St. Armand's Circle. It could not be located more ideally!

Jan 21 – 28

R2,346 ZAR per night

Guest favorite

Home in Venice

4.93 out of 5 average rating, 107 reviews

A Dream Come True

Located in a desirable community of Venice Garden in a quiet neighborhood where you can't tell if it is a weekend or a weekday. The kitchen is fully equipped, beds are amazingly comfortable, the reclining couch and loveseat are great for relaxing. Everything you need for the beach is included in the rental. The private fenced in backyard allows you monitor your pet while enjoying a cup of coffee. Enjoy a guest Netflix account and high-speed internet from XFINITY all included in the rental.

Aug 26 – Sep 2

R2,606 ZAR per night

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 113 reviews

Sweet Siesta Suite

Sweet spot with the best of both Sarasota and Siesta Key - your private oasis for relaxing and rejuvenating. Whether you choose to chill or find adventure it is all within reach! Siesta Key beaches, Village with shops, restaurants, and bars; Sarasota culture, arts, and entertainment; quaint Gulf Gate shops and eateries ...the possibilities truly are endless. Regardless of how you choose to spend your time here, you will be sure to create lasting memories to share and leave wanting more.

Jul 16 – 23

R2,343 ZAR per night

Guest favorite

Home in Venice

4.89 out of 5 average rating, 161 reviews

Venice Pool Villa with Bikes Kayaks Great Beaches!

Relaxing pool home with 2 bedrooms, 1 king bed, 1 queen bed, 1 sofa double bed and one single foldout bed. 2 bathroom pool home just a 8 minute ride away from Manasota beach. Venice beach and caspersons beaches close by too. A great selection of restaurants and plenty of shopping and convenient grocery stores just 5 minutes away!. Also close to bike trails with two FREE bikes at the house and FREE kayaks too. My home is great for everyone! Pets welcome with pet fee, large fenced yard!

Sep 21 – 28

R2,814 ZAR per night

Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 111 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Newly renovated cozy home with all new furnishings and appliances. 2 bedrooms 1 bathroom with an eat in kitchen, sun room, and comfy living room. Stream shows or work virtually with our high speed WIFI. Grab the beach chairs and umbrella to enjoy Lido Key or Siesta Key Beaches both within a short drive. Wind down & grab drinks/dinner in downtown Sarasota or relax in the backyard. Several golf courses near-by or catch Orioles spring training at Ed Smith stadium within walking distance.

Jul 14 – 21

R2,334 ZAR per night

Guest favorite

Home in Sarasota

4.87 out of 5 average rating, 204 reviews

The Pineapple Suite.Teal tropical home in Sarasota

This is a perfect space for a vacations, snowbirds, visiting professionals (desk and work station within home), or families looking for a home located in the center of Sarasota, Florida. Access everything you need in just a short ride: beaches, University Mall/UTC, hospitals, interstate, gyms, downtown, yoga, local hangouts, and really good food! [*Important note: For all communication, please use the Airbnb App. It is the fastest, most direct and effective way to reach us!]

Aug 4 – 11

R1,777 ZAR per night

Guest favorite

Guest suite in Venice

4.81 out of 5 average rating, 114 reviews

Venice large Studio Near Manasota Beach, King Bed.

We are located 8 min from the Manasota beach on a beautiful 1.6 acre property with big shady oak trees. We have everything that you would need for a vacation and for the beach. Just renovated with a modern touch . Comfy King size bed, fully equipped kitchen with a small convection cooktop, beautiful bathroom with walk in shower and even a walk in closet! Ready for beach, umbrella buggie board & chairs. You will TOTALLY LOVE your stay with us!

May 14 – 21

R1,763 ZAR per night

Guest favorite

Cottage in Nokomis

4.98 out of 5 average rating, 123 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Bella Vita! (The Good Life!)…that feeling when you wake up each day in this little slice of Paradise. This is the spot to enjoy a warm peaceful getaway from the rest of the world...just arrive with your bathing suit/flip flops and walk 1.5 blocks to the warm Gulf waters. Tranquillity of beach life, beautiful sunsets and lazy days of fishing and bird watching. Visit the Jetties, where you can see dolphins, manatees and rays, is only 1/2 mile away.

Aug 11 – 18

R2,300 ZAR per night

Guest favorite

Bungalow in Englewood

4.96 out of 5 average rating, 169 reviews

TROPICAL OASIS, MINUTES FROM THE BEACH!!

This charming 2 bedroom/2 bathroom, dog friendly home in Englewood is located 2 miles away from our beautiful Manasota Beach. Call this your home away from home, as you will find a flat screen TV, Dish, free wireless internet and a gas grill, washer/dryer, and a fully equipped kitchen. Bring your boat (boat ramp is located in the neighborhood), bathing suits, beach towels and sunscreen. We have the rest ready for you.

Oct 15 – 22

R2,212 ZAR per night

Guest favorite

Guesthouse in Sarasota

4.86 out of 5 average rating, 370 reviews

The Cottage, very close to Siesta Beach!

The cottage was built in 1926 and is in a Historic Neighborhood. Our location is a 10 min car ride or 25 min bike ride to the #1 Rated Siesta Key Beach and a short stroll to popular eateries and shopping areas. The cottage is cozy and has all the essentials of home. Private entrance, backyard, kitchenette with a full fridge. Ideal for 2 people but can accommodate more. Dogs welcome

Dec 14 – 21

R2,194 ZAR per night