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

The Velvet Blue house 3/2+Pool+5 min Siesta Key
The house looks exactly like the pictures! It was amazing . The house was so beautiful and so clean! Edina , Doris and joe the maintenance guy were very responsive and helpful. The house is on a quiet road . The pool was beautiful especially at night . The house is very close to siesta key beach and there’s so much more all near the home . I would Recommend this house and I will definitely be coming back :) it was a good experience.

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. Shark’s and Pop’s were our favorite restaurants long with Dunkin most every day and DQ once a week Detwiler’s 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 can’t wait to go back . Frank, Sue and Paisley.

2bed/2bath with POOL house, close by SIESTA KEY!!!
We absolutely loved our stay here! The house is beautiful and has everything we needed for vacation. The pool was perfect for the kids - they preferred staying home at the pool than going the beach. Romulda was also so helpful and responsive to all our questions. We only wished we had more time to stay here! We’re looking forward to booking again in the future!

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!

Azalea Sanctuary
We enjoyed our stay at this quaint home! Light switches and cabinets are labeled which was helpful. We’d stay here again for another quick trip to the area.

Casa Playa Sleeps 6
The house was perfect for our small family of three and two dogs! The fenced in yard was wonderful and the location was perfect. The neighborhood is quiet with very low traffic. Only a short drive to Siesta Key, downtown, and other attractions.

Welcome to Paradise Palms! Canal home/Pet friendly
This house was perfect for traveling divers. plenty of room for gear and places to rest. the back patio was great for morning coffee and evening dive briefing. super clean and the best part. 1 TV. lol if you're watching TV, you are missing all the fun. loved this place and will definitely look it up for my next visit

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

Luxury 3/3 with Heated Pool, Spa, & Putting Green!
My wife and I had a great time at this stay. Lots to do at the house along with great beaches and restaurants within a 15-20 minute drive. The house was clean and had everything that you might need. We were able to drive to Disney in just over an hour and a half which provided a different experience to go along with the daily beach/pool trips. Cool AC inside to combat the humid 88 degree weather in June 2025.

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!

Lovely 2 bedroom condo with pool & tennis courts
This condo was even cuter in person than it was in the photos. It was super clean, safe, spacious, had a gorgeous screened in balcony that looked out over the pool, and was centrally located really close to groceries, restaurants, multiple beaches, and more. We stayed here as a family of 4 and the kids had their own room and bathroom and we had a master with en suite. I saw another review that said there is a little noise from the busy road outside but you really only notice it if you're trying to sleep with the windows open. We originally booked a hotel that ended up being awful so I found this place last minute and they were able to get us in the very next morning. They let us check in early since we were kind of stranded, and walking in was like a breath of fresh air. Highly recommend this place for 2-4 people!

A Hidden Gem in Paradise
Diana’s 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 apartment’s closet. Also there is a safe in the bedroom which made us feel protected. We are definitely very happy that we stayed at Diana’s place and can recommend it to anyone who wants to come to Sarasota for the holidays.

Sunshine Inn Paradise
Visited from TN and had an awesome stay! Ron is a supremely chill host. Definitely recommend this BnB and would book again if I were in the area

Tropical Oasis Pool Home 1 mile to the Beach
Cory was a wonderful host. When we called to inquire about the temperature of the pool water (it felt cold to us, after the heater was turned on,) Cory was very responsive and made arrangements for someone to come over right away to turn it up for us! Thanks for accommodating our request and for your concern that we were comfortable and had everything we needed for our stay in Florida.

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI
Great place to stay !! The house is beautiful, it’s in a great location and I love the pool area, I had so much fun with my friends on this trip and we’re planning to come back !!

Tropical Retreat Close to Beaches |Pool |Game room
Absolutely loved our stay! The house looked exactly like the photos—beautiful, bright, and well-kept. Everything was spotless when we arrived. The host went above and beyond by providing tons of beach equipment, which made our beach days so easy and fun. The location was perfect—just a short walk to the marina, but tucked away in a quiet, peaceful area. Communication was seamless; the host was super responsive and helpful throughout. Would definitely stay here again and highly recommend it to anyone visiting the area!
Private, pet-friendly home rentals

Last minute June ,House 2 Mil beach .Pets welcome
Great location, clean and cute. A great size for a large or small group of people

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.

Short walk to beach 4, King bed, Dog Friendly
Loved this spot! You can’t beat the location! I would recommend staying here if you want to spend everyday at the beach. 😎🏖️

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!

Beach house
Airbnb review: Not only is the location perfect for beach goers looking for shark teeth (we had more luck in Nokomis than Venice beach), but the house comes fully equipped with everything anyone needs to make this place a home away from home. We are avid cooks and were able to utilize the kitchen (and the spices were not just salt and pepper)! Additionally, the beach supplies in the shed are abundant. We didn’t have luck with the beach buggy, but they supply you with good quality towels, linens, blankets, etc. The office is also a nice touch for those who need to work remotely because it has a door and is nicely lit. The backyard space is perfect for families and friends. Overall, as people who have airbnbed a lot (since we prefer to have a kitchen), this was a perfect hidden find. Jaime was also a great host and will be sure to look out for items you may have left behind. Next time we go to Nokomis, we will plan to use the same airbnb. Thank you, Jaime!

1 Bed 1 bath 7 mins to the beach
Near Siesta Key, a quiet neighborhood. The house has everything you need to cook and be comfortable. Keep in mind that if there are more than two people, the third must sleep on an inflatable mattress (very comfortable, but to be taken into account). My son slept very well there.

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!

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
$116 NZD 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
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Jannus Live
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Myakka River State Park
- Alafia River State Park
- South Jetty Beach