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

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!

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.

Renovated, Cozy 2 Bedroom
Location is perfect. Very clean and Tomas is great with communication! I will be back đ

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!

Lake Front House with a Pool
This house was spotless, organized and had a loaded kitchen! It is in a amazing location near the beaches and the house came loaded with beach equipment. I would love to come back. Birute was very helpful with us and responsive in timely manner Thansk for all!

Home near Lido Beach - Hot Tub + Fire Pit
Jacob was an accommodating and informative host. He provided recommendations and checked in a few times which was appreciated. The guest house is small, clean, and as described. The location is quiet, albeit about a 20 minute drive from most of the beaches and downtown Sarasota where we spent most of our time. The drive was easy and there are lots of places nearby to get what you need.

Mid-Century Oasis with Pool in Arlington Park 1
This place is perfect. Everything you want in an air bnb and itâs exactly like it looks. My family and I were beyond happy with it. The pool is gorgeous. The location is amazing itâs legit 8 to 10 minutes away from pretty much anything you need or want to do. The house is quiet and the beds are super comfy. I would rent this place every year for a trip. Also the host is awesome! They were there for anything we needed or had questions about and are super nice and friendly people. Thanks again for everything!

A Dream Come True
This home was great for us and great location, thank you for letting us stay!
Pet-friendly home rentals with a pool

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 weâre in town.

SunshineVilla/Pool/spa/beach /luxury/new
Inessaâs home in North Port was absolutely stunning! The house was pristine, with a quaint and beautiful layout, spotlessly clean. The pool was a magnificent highlight, and the home was well-equipped with plenty of towels, washcloths, coffee, tea, silverware, dishware, and cooking utensils. They even left water in the fridge for us! The king-size bed and pillows were incredibly comfortable, making our stay even better. Shops were close by, and Inessa was super responsive and easy to reach. We highly recommend this gem if youâre looking for something very nice and cozy! We canât wait to come back! â Thank you Inessa â¤ď¸ Larry & Michelle

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

Slice of Paradise in Nokomis
A Slice of Paradise was amazing. Robert was a GREAT Host , he answered every question with in hours, if not minutes. Great location and close to everything. After a couple days it felt like home, when our 6 weeks were up we did not want to leave. We hit 7 different beaches and some 3 or 4 time each. Sharkâs and Popâs were our favorite restaurants long with Dunkin most every day and DQ once a week Detwilerâs Farm Market on Tamiami Trail was our go to for fresh fruits and vegetables. Their bakery was wonderful. We would highly recommended A Slice of Paradise. We canât wait to go back . Frank, Sue and Paisley.

A Hidden Gem in Paradise
Dianaâs place is a very comfortable. Very clean, cozy, with a fully equipped kitchen, stove, dishwasher, large refrigerator, washer and dryer. There is a private barbecue area and a reserved parking space. 10 minutes by car to Siesta Beach and 13 minutes to Turtle Beach. We found a beach umbrella and chairs in the apartmentâs closet. Also there is a safe in the bedroom which made us feel protected. We are definitely very happy that we stayed at Dianaâs place and can recommend it to anyone who wants to come to Sarasota for the holidays.

Royal Coachman Resort - bay oasis near beach
Robâs 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!!

Private Siesta Beach House Oasis with Heated Pool.
Great place, we enjoyed the house so much, my wife and I really enjoyed it but our 15 yr old dog got a post vacation depression after being at this house. He was so happy and so were we. Great location, the house has everything you need to disconnect and enjoy few days by the pool. Andrew is a very quick responsive host. Perfect place, perfect days!

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

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 đ We enjoyed our stay and would love to come back.

Short walk to beach 4, King bed, Dog Friendly
Loved this spot! You canât beat the location! I would recommend staying here if you want to spend everyday at the beach. đđď¸

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.
Jaredâs 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 nightâsuper spacious and comfy! Definitely recommend.

Suite Spot in Gulf Gate
Great little Airbnb - perfect for what we needed for a long weekend in Sarasota. The suite was spotless, easy to get to, and in a great location with excellent restaurant options within walking distance.

JUNE. SALE! Beach Sarasota, NEW Villa,Yard Pets OK
Our family had a wonderful stay - would definitely stay here again. It was 3 minutes to Nokomis beach - lots of shells and beautiful water. Took us with two toddlers 20 minutes to walk there. Only 8 minutes to Venice beach. The screened in porch was key with our two toddlers. Shower was very nice and the bed was comfortable. Kitchen cooking supplies were plenty stocked. Thank you for hosting us!

Serenity in Venice! Steps to Shamrock Park & Trail
Great communication! We love the house; a lot of entertainment. My teenage son was in love with the old disc music player. Grateful for the opportunity to use your home.

Casa Azul a beach oasis! (Pet friendly Duplex)
Our stay at Casa Azul was fantastic. The home was cute & clean and had everything we needed- plenty of clean towels, basic toiletries & laundry soap, and beach gear! And it's an easy walk to Pop's and the beach! Roger & Claudette were great hosts. I definitely recommend Casa Azul
Quick stats about holiday rentals that are pet-friendly in Osprey
Total rentals
30 properties
Nightly prices starting at
$90Â 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