
Pet-friendly holiday 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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Popular amenities for Osprey pet-friendly home rentals
Pet-friendly house rentals

2 BR House 1.6 miles from Siesta Key Beach
This home was amazing and loved it, host was very nice and responded quickly every time.

Perfect location updated & loaded with all u need!
Would recommend highly! Great location (everything is working a 10-15 min drive at the most). The place itself is very cozy and plenty of space for the four of us that resided there for the weekend. Definitely would stay here again if I find myself in the area again.

The Pineapple Suite.Teal tropical home in Sarasota
Loved the place and no complaints whatsoever, I’ll be there again

Azalea Sanctuary
Needed a place to stay while my house was being worked on. Raymond was very accommodating. I would definitely stay here in the future!

On the water in Venice FL.
Jared’s house is ideal for a people who like to go to the beach. It had all the beach gear and is about 10 minutes from Venice and Nakomis beaches. The neighborhood is quiet and the sunset view is the best! The couches are great for movie night—super spacious and comfy! Definitely recommend.

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI
This was a great home for our family of six. We hope to return again.

10 minutes to SiestaBeach Barefoot Bliss Bungalow
Fabulous stay at Katya’s…perfect place to practice rest-n-relaxation techniques…out the door to the left for walk on the wild side…out the door to the right and life’s a beach…will definitely keep on top of list for places to stay & play ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks
If you’re looking for the perfect Airbnb for fishermen and vacationers are alike, this is it. This Home is elegant and extremely clean. The host are responsive and so sweet and kind. It has everything you can need , and it’s in the perfect location. We loved relaxing and watching the rain in the Florida room. We really enjoyed all the nature outside and fishing from the dock so many memories were made with our family here.
Pet-friendly home rentals with a pool

Luxury 3/3 with Heated Pool, Spa, & Putting Green!
Erinn was an amazing host - she would respond immediately to any text and was always friendly and helpful. The house is as good as it looks if not better! My husband complains about every airbnb I book but he even he had to admit this one was top notch.

Pool, Spa, & Private Gym in the Heart of Sarasota
We had a great stay at the house. Loved the interior decor. Looks like the home was remodeled recently. Everything was fresh and clean. We loved hanging out by the pool. Backyard was very private and peaceful. Posts were very quick with their responses if I had any questions about the home. We would definitely stay at the Home again when we’re in town.

Free Early Chk-in, Super Clean, Free Parking,Bikes
We had a great stay at Lisa’s. It was well stocked and had everything we needed for a great stay. Would definitely recommend!

Charming Home in Sarasota-8min from Siesta Key
The hosts were very responsive and very helpful. Their home was spotless. The pool with the enclosure allowed you all the sunshine you could ask for without the bugs! The interior is very spacious and great for hosting dinner. With the turf back yard it’s the perfect hangout for adults and children! The hosts are very thoughtful with items available for the perfect beach day (beach wagon, chairs, a cooler, and lots of fun items for children! We will definitely be visiting again!

Royal Coachman Resort - bay oasis near beach
Rob’s house was great! Great location to restaurants and the beach. And 10 mins to Fox Lea Farm if you are going to show!! If I had a question he responded right away. Very clean and nice! Would definitely stay again!!

Oz Cottage hot tub, Pool, 2.9 m beach
Loved my stay with Te. She’s amazing and so is her place. The courtyard is so soothing with nature’s beauty. Close to the beach too! Hope to be back soon 😌

🌟Venice Cute Pool Villa with bikes Kayaks 🌈🐬
We had the best stay here! Lucky was quick to respond to any questions we had and the space was clean and well taken care of, it made for a relaxing trip!

Downtown Apartment w/ Pool, Gym, & Coworking 329
Great place, would stay again!
Private, pet-friendly home rentals

The Cozy Bungalow: Sleeps 4, private patio & grill
The hosts were super friendly and quick to respond to any questions we had. The house was in great shape and appeared to have been recently renovated. Everything was squeaky clean down to the vacuum lines in the sofa. If you plan to make a trip to the beach, they have provided beach chairs, umbrella, football, sunblock, etc. The neighborhood was quiet and easy to find. I would recommend anyone visiting Sarasota to check this place out. Definitely 5 stars!!!

Good Beach Bungalow
My family of 4 recently had a wonderful stay. The house was beautifully appointed, perfectly clean, and well stocked. It is located very close to a great bike trail and we used the bikes that were provided by the hosts. The house also had beach chairs, toys, and a shark tooth sifter for guests to use. The beds were our favorite part and everyone slept wonderfully!

Walk to the beach from this lovely 2 bedroom condo
This place is awesome! A nice washer and dryer, super clean, comfortable, and a cute outside sitting area. host left snacks, water, cooler, flashlight, and beach towels - very well thought out. The host was also super nice when we thought we locked ourselves out 😅 We enjoyed our stay and would love to come back.

2Bed/1Bath Entire House Mins to Beach+Downtown
This house was adorable! Loved the decor - cute touches and uncluttered throughout. Drawers/cabinets were clearly labeled and there were all sorts of things there that you might have forgotten- even hair ties! Bed was comfortable. Whole place was cozy and comfy- I didn’t want to leave! Tons of great recommendations in the guest book by the front door. I wholeheartedly recommend this home!

Luxury Pet friendly home, 2.7miles to Siesta Key!
We had a wonderful stay at this property. We were in town for our son's sporting event for several days. It was exactly as described and more. It was clean and comfortable and there were so many "extras" that we do not usually experience in other rental properties. The kitchen was fully stocked with utensils, cooking supples, spices, coffee, and more (better than any rental we've stayed in). There is not one negative thing I can say about this place or the host. Honorata was extremely responsive and helpful and allowed us to check in early, which we greatly appreciated as we needed to drop our luggage and go to an event. The location was great, a short drive to the beach, stores, etc. and the neighborhood was quiet and felt safe. We would highly recommend this property and hope to stay there again next time we are in the area. Thank you Honorata and Conrad for a lovely stay!

Hidden GEM Sarasota Siesta BEACH
The home is simply beautiful, open, airy, Clean the backyard and pool are beautiful and so private. Hidden Gem is a perfect name for this home as you would never expect to find a home like this on a ‘such a typical’ block. It’s like brand new. Everything is updated and modern. The bathrooms and showers were clean and beautiful. Large TV in the living room with comfy couches (a bit worn) but still comfortable. We all loved the place! Would stay again in a heartbeat! So quiet and peaceful.

Venice Gardens, 2-Br Pet Friendly Home - Indra
This truly felt like home away from home. Very clean, cozy home in a quiet neighborhood. Our 2 dogs and toddler enjoyed the fenced in backyard. The air conditioner works great! We loved sitting out in the lanai listening to the birds. We felt very safe here and Tom was very responsive. 🥰

"The Boho" Horse Ranch w/ Barnyard friends
Dawn and Pat could not have been more accommodating and wonderful as hosts! The property is simply extraordinary, and they go above and beyond to make it feel like your own home away from home. The animals are adorable and super fun!!! I travelled to Florida with my special needs son, and two silly pups and it was so wonderful. Thank you Dawn, we will be back!!!
Quick stats about holiday rentals that are pet-friendly in Osprey
Total rentals
30 properties
Nightly prices starting at
$90 SGD before taxes and fees
Total number of reviews
380 reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Anna Maria Island
- Siesta Beach
- Captiva Island
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- North Beach At Fort DeSoto Park
- River Strand Golf and Country Club
- Myakka River State Park
- Alafia River State Park
- North Jetty Beach