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Pet-friendly holiday rentals in Osprey

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Osprey pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Sarasota
4.94 out of 5 average rating, 71 reviews

2 BR House 1.6 miles from Siesta Key Beach

MaryRating, 5 stars3 weeks ago
This home was amazing and loved it, host was very nice and responded quickly every time.
Guest favourite
Home in Nokomis
4.88 out of 5 average rating, 26 reviews

Perfect location updated & loaded with all u need!

AleishaRating, 5 stars3 weeks ago
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.
Superhost
Home in Sarasota
4.83 out of 5 average rating, 240 reviews

The Pineapple Suite.Teal tropical home in Sarasota

mohsenRating, 5 stars3 weeks ago
Loved the place and no complaints whatsoever, I’ll be there again
Guest favourite
Home in Port Charlotte
5 out of 5 average rating, 12 reviews

Azalea Sanctuary

JeremyRating, 5 stars1 week ago
Needed a place to stay while my house was being worked on. Raymond was very accommodating. I would definitely stay here in the future!
Guest favourite
Home in Nokomis
5 out of 5 average rating, 13 reviews

On the water in Venice FL.

AngelaRating, 5 stars2 months ago
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.
Guest favourite
Home in Bradenton
4.92 out of 5 average rating, 369 reviews

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

BettyRating, 5 stars2 days ago
This was a great home for our family of six. We hope to return again.
Guest favourite
Home in Sarasota
4.96 out of 5 average rating, 134 reviews

10 minutes to SiestaBeach Barefoot Bliss Bungalow

ChrisRating, 5 stars1 month ago
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 ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
Guest favourite
Home in Venice
4.95 out of 5 average rating, 141 reviews

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks

KatieRating, 5 stars2 weeks ago
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

Top guest favourite
Home in Sarasota
5 out of 5 average rating, 60 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

KristinRating, 5 stars5 days ago
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.
Guest favourite
Home in Sarasota
5 out of 5 average rating, 6 reviews

Pool, Spa, & Private Gym in the Heart of Sarasota

NatalyaRating, 5 stars1 week ago
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.
Guest favourite
Flat in Indian Beach-Sapphire Shores
4.96 out of 5 average rating, 140 reviews

Free Early Chk-in, Super Clean, Free Parking,Bikes

VictoriaRating, 5 stars2 weeks ago
We had a great stay at Lisa’s. It was well stocked and had everything we needed for a great stay. Would definitely recommend!
Top guest favourite
Home in Sarasota
4.98 out of 5 average rating, 51 reviews

Charming Home in Sarasota-8min from Siesta Key

KhloeyRating, 5 stars2 weeks ago
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!
Guest favourite
Cabin in Nokomis
4.95 out of 5 average rating, 20 reviews

Royal Coachman Resort - bay oasis near beach

BitsyRating, 5 stars1 month ago
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!!
Top guest favourite
Flat in Englewood
4.95 out of 5 average rating, 414 reviews

Oz Cottage hot tub, Pool, 2.9 m beach

AretiRating, 5 stars2 weeks ago
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 😌
Guest favourite
Holiday home in Venice
4.85 out of 5 average rating, 138 reviews

🌟Venice Cute Pool Villa with bikes Kayaks 🌈🐬

ChelseaRating, 5 stars5 days ago
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!
Guest favourite
Flat in Downtown Sarasota
4.89 out of 5 average rating, 156 reviews

Downtown Apartment w/ Pool, Gym, & Coworking 329

JaredRating, 5 stars2 weeks ago
Great place, would stay again!

Private, pet-friendly home rentals

Guest favourite
Flat in Sarasota
4.93 out of 5 average rating, 15 reviews

The Cozy Bungalow: Sleeps 4, private patio & grill

LorenRating, 5 stars1 month ago
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!!!
Guest favourite
Home in Nokomis
5 out of 5 average rating, 5 reviews

Good Beach Bungalow

KateRating, 5 stars2 months ago
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!
Superhost
Apartment in Nokomis
4.94 out of 5 average rating, 18 reviews

Walk to the beach from this lovely 2 bedroom condo

Tiffany HopeRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Sarasota
4.9 out of 5 average rating, 96 reviews

2Bed/1Bath Entire House Mins to Beach+Downtown

ElizabethRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Sarasota
4.99 out of 5 average rating, 69 reviews

Luxury Pet friendly home, 2.7miles to Siesta Key!

CarenRating, 5 stars5 days ago
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!
Superhost
Home in Sarasota
4.82 out of 5 average rating, 11 reviews

Hidden GEM Sarasota Siesta BEACH

ChristaRating, 5 stars3 months ago
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.
Guest favourite
Home in Venice
4.85 out of 5 average rating, 55 reviews

Venice Gardens, 2-Br Pet Friendly Home - Indra

TaraRating, 5 stars1 month ago
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. 🥰
Top guest favourite
Farm stay in Sarasota
5 out of 5 average rating, 13 reviews

"The Boho" Horse Ranch w/ Barnyard friends

ShelleyRating, 5 stars1 week ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Osprey
  6. Pet-friendly rentals