Vacation rentals with a pool in Osprey

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Popular amenities for Osprey rentals with a pool

House rentals with a pool

Guest favorite
Home in Nokomis
4.87 out of 5 average rating, 54 reviews

Luxury Oasis Home 3BR 2Bath with Heated Pool

JaclynRating, 5 stars1 month ago
Fantastic location if showing at Fox Lea. House was exactly as photographed and very comfortable.
Guest favorite
Home in Nokomis
5 out of 5 average rating, 25 reviews

3-bedroom home with pool

MarineeRating, 5 stars4 weeks ago
Marilyn was very responsive when I needed her, and the place looked exactly like the pictures posted. It’s only 8 minutes driving to Nokomis Beach and same for Downtown Historic Venice where you can find all the good local places to eat and buy gifts, as well as Venice Beach at the end of downtown . Publix is very close if you need to buy groceries. Everything was provided at the house, even things for the beach. The house was beautiful and the location was great and quiet. The pool didn’t disappoint. My grandkid loved it . We all did. I recommend 100% this place! Spacious, clean, beautiful and convenient. If it’s available in the future I will stay here again.
Top guest favorite
Home in Sarasota
4.98 out of 5 average rating, 51 reviews

Charming Home in Sarasota-8min from Siesta Key

KhloeyRating, 5 stars3 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!
Top guest favorite
Home in Sarasota
5 out of 5 average rating, 102 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

CamilaRating, 5 stars4 weeks ago
We really enjoy to stay at the house that is perffect spot to relax is a quiet neighborhood. We'll definitely recommend and came back soon.
Top guest favorite
Home in Nokomis
4.98 out of 5 average rating, 47 reviews

The Pineapple Escape

ErinRating, 5 stars1 week ago
Our family had a wonderful stay at Claudia's home! She is a very friendly and responsive host. The neighborhood is quiet and in a central location to many wonderful beaches and restaurants. The house and pool were very clean and stocked with many kitchen, bathroom and pool essentials. We definitely recommend the Pineapple Escape!!
Guest favorite
Home in Sarasota
4.94 out of 5 average rating, 18 reviews

Siesta Key Modern Retreat with Heated Pool & Spa

AnnRating, 5 stars2 months ago
The house was tucked into a quiet residential community. The home was clean, fresh and spacious. The guest house area with its own bathroom is perfect for a two family stay! The neighborhood was safe to walk in- I walked daily. The neighborhood was really within 15 minutes drive of anything we wanted to do. We spent most of our time at Siesta Key! Leave EARLY for the beach, if that's your day's plan! We would definitely stay again!
Guest favorite
Home in Sarasota
4.97 out of 5 average rating, 86 reviews

3 bedroom Heated salt water pool close to Siesta

KristoferRating, 5 stars3 days ago
Very beautiful home! Great place to stay and enjoy as well as just close enough to Siesta Keys beach! Peaceful and very clean!! Definitely a must stay!!
Guest favorite
Home in Sarasota
4.97 out of 5 average rating, 29 reviews

Right on the bay! Heated pool! King bed

DavidRating, 5 stars1 month ago
We had a awesome stay, sergiy was excellent in communication his home is beautiful and very clean. Book this place you will NOT regret. Thanks Sergiy

Condo rentals with a pool

Guest favorite
Condo in Siesta Key
4.91 out of 5 average rating, 127 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

MariaRating, 5 stars2 weeks ago
Loved the location and the layout of the condominium! We will be coming back!
Top guest favorite
Condo in Siesta Key
4.97 out of 5 average rating, 320 reviews

On the Beach; Siesta Key SunBum Studio

AlexRating, 5 starstoday
This wasn’t our first time at the Sun Bum … it’s the perfect get away spot. As close to the beach as you can get, has everything you need, and the hosts are BEYOND accommodating. We came for our birthday and they had a birthday banner hung on the wall waiting with a bottle of prosecco. They really make you feel special! If you’re looking for a wonderful spot for you and your spouse, this is the place!!
Superhost
Condo in Lido Key
4.8 out of 5 average rating, 104 reviews

LIDO KEY 1 BR/1Bath Heated Pool 16

ChrisRating, 5 stars9 months ago
Had a great stay and everything was as listed. Clean and convient, quiet location, 5 minute walk to the beach. Was located right across from both pool and laundry room (quarters only) which was great. William also provided beach chairs and umbrella as well as small cooler which was exactly what I needed
Guest favorite
Condo in Sarasota
4.86 out of 5 average rating, 149 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

AnnRating, 5 stars3 weeks ago
Great stay, the location, the amenities all were wonderful. Melissa and Brandon were super responsive and the place had more essential stocked than most of the other places we have stayed, which was very thoughtful. Melissa also had a regular coffee pot sent out to us right away, since we don’t use Keurig’s which was super nice and very much appreciated. We would definitely come back!
Guest favorite
Condo in Bradenton Beach
4.88 out of 5 average rating, 121 reviews

Charming and Updated 1 Bedroom in Runaway Bay

MeleahRating, 5 stars3 weeks ago
My fiancé and I really enjoyed our stay at David’s place in Bradenton! The space was super clean and had everything I needed for a comfortable stay. Communication was excellent throughout; the host was responsive, helpful, and always timely with their messages. One of the best parts was the beach access—super convenient, and the place was stocked with everything from a beach cart, umbrellas, chairs, and beach towels etc. which made days at the beach so easy. There were also a few great local tips provided, which I definitely took advantage of. Honestly, I wouldn’t change a thing. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a wonderful stay!
Top guest favorite
Condo in Longboat Key
4.98 out of 5 average rating, 186 reviews

Condo with a View 1: Open Friday, $250/nt!

AbigailRating, 5 stars1 week ago
This condo was everything I needed and more! The location? Absolutely perfect—the beach is literally your backyard. Waking up to that ocean view the next morning was a dream. Restaurants and activities were just minutes away, which made everything so easy and fun. Heidi, the host, went above and beyond. Her communication was fast, kind, and incredibly thoughtful. She even surprised us with a delicious key lime pie and orange juice waiting for us after jet skiing—such a sweet and personal touch! I truly have no complaints. Everything about this stay was peaceful, beautiful, and seamless. I’d absolutely recommend this spot to anyone looking for a relaxing and magical beach getaway. 🌴🌊💛
Guest favorite
Condo in Siesta Key
4.94 out of 5 average rating, 109 reviews

Siesta Key Beach Front Condo

JenniferRating, 5 stars2 weeks ago
Another wonderful trip to Siesta! This is our third stay in one of Evan’s places, and we were not disappointed. This unit had a great view of the Gulf (this particular building has the most direct view, without the parking lot!), and the screened in lanai was amazing! As always, the unit was clean, well-stocked, and a perfect home away from home. Already counting down the days till we return!
Top guest favorite
Condo in Bradenton
4.98 out of 5 average rating, 206 reviews

Shorewalk full condo IMG Beaches Anna Maria

FrankRating, 5 stars1 week ago
I've stayed in Shorewalk 4 different times now, but you're place has been the best, by far. Super clean and accommodating. Great communication and always quick to respond. Thank you!

Quick stats about vacation rentals with a pool in Osprey

  • Total rentals

    50 properties

  • Nightly prices starting at

    R1,070 ZAR before taxes and fees

  • Total number of reviews

    390 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • 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. Rentals with pools