House in Osprey, FL
10 guests · 4 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
Escape to our 4-bed, 2.5-bath Pool Home on exclusive Casey Key Island. Home to many celebrities , our retreat accommodates 10 comfortably. Experience island living, pristine beaches, and upscale comfort. Your paradise awaits! This home is equipped with everything you will need for you vacation.
We also Include a golf cart to enjoy and tour the beautiful homes, tiki bars, beach, and restaurants by the island.
Casey Key is located just south of Sarasota. It's close to tons of waterfront restaurants, shopping, Public Beach is a short golf cart drive away, and you are also nearby the beautiful Siesta Key Beach. Maps state we are walking distance and we are not walking distance to the beach. However, you can walk to an inlet by the bridge and rent kayaks and paddle-boards. This is just around the corner from the house.
Side note: We do allow pets for an additional pet fee of $250, should your pet cause any extra cleanup needed upon check-out, we reserve the right to charge an additional cost for the clean or damages. This is on a case by case basis. If you’re bringing a pet with you, please add pet to your reservation.
We also Include a golf cart to enjoy and tour the beautiful homes, tiki bars, beach, and restaurants by the island.
Casey Key is located just south of Sarasota. It's close to tons of waterfront restaurants, shopping, Public Beach is a short golf cart drive away, and you are also nearby the beautiful Siesta Key Beach. Maps state we are walking distance and we are not walking distance to the beach. However, you can walk to an inlet by the bridge and rent kayaks and paddle-boards. This is just around the corner from the house.
Side note: We do allow pets for an additional pet fee of $250, should your pet cause any extra cleanup needed upon check-out, we reserve the right to charge an additional cost for the clean or damages. This is on a case by case basis. If you’re bringing a pet with you, please add pet to your reservation.
Amenities at Island Pool House on exclusive Casey Key in South Sarasota.
Non-smoking
Pets allowed
Family friendly
Map of Osprey, FL
Ratings and reviews
10 / 10Outstanding·May 2026
We had a wonderful time staying at Casey Key!
10 / 10Outstanding·Apr 2026
Our three-night stay was as promised with comfortable relaxing spaces for our family and guests. We enjoyed conversations in the living room and dining on the back patio while many family members, including two young grandchildren, enjoyed the hot tub, pool and slide! Our time there included sunsets nearby, rides in the golf cart and a day on Nokomis Beach, just 15 minutes from the home. The home worked out very well for our three generation stay
10 / 10Outstanding·Apr 2026
Property was a great location, easy check in and great communication with Olivia. Had some minor issues but nothing to make stay uncomfortable. Would recommend this property for nice beach stay. Thank you Olivia for taking care of issues in Timely manner. Steve
6 / 10Average·Oct 2025
We arrived to a clean interior, but many issues that should have been fixed prior to renting. Broken toilet on the bottom floor, outlets not working, door handles missing to the pool deck, cob webs covering the entire pool deck, and a green pool full of algae. The host requests that you don’t communicate through the app, however their property manager took hours to respond and at first claimed we were lying because she was there the day prior. A handyman and pool company came out on day 2 of our stay, but we couldn’t swim until after 7pm due to chemicals and they fixed “most” of the other issues. When we shared our frustration, the host eventually said our only option was to leave the property and go somewhere else. Which truthfully, was a frustrating response because we were there to celebrate my mom’s 50th birthday. We spent 2 of our 3 days facilitating getting these issues resolved. It just wasn’t ideal. The house itself was great and the stay ended up being fine, but the condition of the property was disappointing. I do also want to point out that there is no drinking water or ice on the property. It’s not a huge deal, but important to know if you’re traveling from out of town! Publix is right down the road but easier when you can plan for it. The listing also shows 2 bikes, there was only 1 & had 2 flat tires & no bike pump. Lots of kids toys & the golf cart was our highlight!Again, not the end of the world but I do think this property was unfortunately overpriced.
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Top rated by guests
8.8Excellent
(22 Ratings)
"We had a wonderful time staying at Casey Key!"
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