Pet-friendly vacation rentals in Osprey

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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

Home in Sarasota

4.9 out of 5 average rating, 146 reviews

Sunshine Suite, Minutes to Beach,Tropical Paradise

The Sunshine Suite.Lots of natural light in this totally updated modern 3 bed/1 bath home.It is a completely separate dwelling w separate entry from the other dwelling on the property sharing no common walls. Smart thermostat & door lock. Keyless entry.Brand new AC, gas oven, quartz counter w/ custom marble backsplash, modern & comfortable furniture, private outdoor area, gas BBQ grill, off street parking.Great location! Minutes to Siesta Key beach, shopping/UTC, interstate, hospital & downtown

Oct 27 – Nov 3

G$19,496 GYD per night

Superhost

Guest suite in Sarasota

4.78 out of 5 average rating, 234 reviews

Sarasota Escape: Perfect Studio Near the Beach

Experience Sarasota like never before in our studio. Immerse yourself in the seaside charm while enjoying the comfort of a home away from home. Perfectly situated in the heart of Sarasota, you'll have easy access to all the must-see attractions, from the pristine Siesta Key beach to the bustling downtown area. Plus, with Sarasota Bay, Marina Jacks, top-rated restaurants, and grocery stores just a stone's throw away, everything you need is within reach. Come live the dream & book your stay today!

Aug 26 – Sep 2

G$22,491 GYD per night

Guest favorite

Home in Venice

4.94 out of 5 average rating, 101 reviews

Dock House w/ 4 Kayaks on the Intracoastal

Welcome to our Mid Century Modern waterfront hideaway! Bring your toys :) Just 5 minutes/2 miles to the pristine beaches. Search the world-famous coast for shark teeth! Get on the water and explore the Gulf of Mexico by kayak or boat. Our dock can accommodate up to a 23’ boat. Have some fun grilling out back over a few games of cornhole along the water. Enjoy fishing from your private dock. We highly recommend taking the bikes for a cruise on the Legacy Biking Trail located steps from the house.

Sep 1 – 8

G$71,586 GYD per night

Guest favorite

Apartment in Sarasota

4.88 out of 5 average rating, 138 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 17 – 24

G$22,225 GYD per night

Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 129 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 26 – Oct 3

G$26,806 GYD per night

Guest favorite

Home in Venice

4.93 out of 5 average rating, 108 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.

Nov 18 – 25

G$28,247 GYD per night

Guest favorite

Guest suite in Sarasota

4.93 out of 5 average rating, 115 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.

Sep 14 – 21

G$23,095 GYD per night

Guest favorite

Home in Venice

4.9 out of 5 average rating, 162 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!

Jun 2 – 9

G$29,660 GYD 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.

Oct 1 – 8

G$22,476 GYD per night

Guest favorite

Guesthouse in Sarasota

4.89 out of 5 average rating, 168 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

Come and enjoy our newly remodeled 400 square foot laid back beached themed guest house. Located just 1.5 miles away from Sarasota/ Bradenton airport, and less than 10 miles away from our world famous beaches. Whether you are a single person in search of a long term stay or a family looking for a short vacation, we have the place for you. Our guest area is attached to our main residence and has a private entrance. Enjoy our shared swimming pool and outside patio areas.

Sep 3 – 10

G$21,204 GYD per night

Guest favorite

Guest suite in Venice

4.8 out of 5 average rating, 116 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!

Jun 19 – 26

G$21,553 GYD 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 21 – 28

G$24,903 GYD per night