
Pet-friendly vacation rentals in Osprey
Find and book unique pet-friendly homes on Airbnb
Quick stats about vacation rentals that are pet-friendly in Osprey

Total vacation rentals
Explore 30 vacation rentals in Osprey

Nightly prices starting at
Osprey vacation rentals start at G$10,443 GYD per night before taxes and fees

Verified guest reviews
Over 630 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Osprey vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Osprey rentals

4.9 Average rating
Osprey stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated pet-friendly home rentals in Osprey
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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 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

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

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.

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

Spacious Gulf Escape 7 min to Nokomis Beach Pets
Sandy Flamingo Vacation Rentals Whether you're traveling for business or leisure, our vacation home is the ideal spot to unwind after a day at the sunny beaches, fishing, boating, or exploring the area. Bring the whole family to enjoy the ample space in our 2,100 sq. ft. home, featuring numerous extras to make you feel at home. Spend relaxing evenings on the large covered and screened porch without the hassle of insects. Our large, open and fully stocked kitchen is ideal for the chef in you.

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!

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.

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.

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!

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.

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
Pet-friendly house rentals

Siesta Breeze ~ Charming Coastal Cottage

Welcome to Paradise Palms! Canal home/Pet friendly

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Oceanfront home w/sunset views of Sarasota Bay

A Dream Come True

Lake Front House with a Pool

Saltwater Oasis
Pet-friendly home rentals with a pool

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

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

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

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Beautiful Home on a prestigious 18 holes golf

Pets, Plunges & Peace on the Gulf of Mexico

Storybook Cottage With Pool Near the Bay & Beach

Luxury Canal Home | Pool, Spa & Dock Near Beach
Private, pet-friendly home rentals

The Nautilus Casita

Viva life Residence

Summer sunset. 3 minutes away from beach!

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

Beach house

Nokomis waterfront unit | Kayaks | Boat Friendly

Florida Gem close to Nokomis Beach & Venice DT

Nirvana In Nokomis
When is the best time to visit Osprey?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$37,178 GYD | G$45,115 GYD | G$40,520 GYD | G$38,431 GYD | G$33,001 GYD | G$33,418 GYD | G$33,627 GYD | G$36,551 GYD | G$33,836 GYD | G$33,001 GYD | G$37,178 GYD | G$36,133 GYD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
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