Vacation rentals with a pool in Osprey

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Top-rated rentals with a pool in Osprey

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Sarasota

4.97 out of 5 average rating, 221 reviews

Your private retreat near Siesta Key Beach.

Your Private Retreat! Nestled at the end of a quiet dead-end street. This distinguished rental property guarantees a relaxing Florida vacation for everyone! Completely remodeled with Coastal-Modern Decor. 3 bedroom, 2 bath, amazing heated pool home and private back yard is located in the Gulf Gate Estate neighborhood. A short drive (less than 2 miles) to the white coastal sands of Siesta Key Beach, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Must be at least 25 years old

Guest favorite

Home in Osprey

5 out of 5 average rating, 29 reviews

Heated Pool | 3 Beds | Near Beaches and parks

This unique home is located on a private street away from the hustle and bustle of the city, yet close to the action. As you pull up to this wooded oasis you will notice the natural vegetation that gives complete privacy to this newly renovated home where every detail has been thought of for the perfect vacation. The cool coastal vibe is sure to impress even the most discerning guests. Pets considered. Please ask! Pre-auth for pet required. Small, non-shedding dogs only. Pet fee of $150 due

Guest favorite

Home in Sarasota

4.94 out of 5 average rating, 332 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

- Located in a quiet Sarasota neighborhood minutes from shopping, restaurants, & Siesta Key, this amenity packed home is perfect for families and beach enthusiasts! - Enjoy the heated pool and new luxurious outdoor furniture in your fenced in backyard where you can bask in the sun swimming and grilling. - Beautifully remodeled coastal interior w/ new appliances, Smart TVs, and fast WiFi. - Your on-site Superhost is available if needed to assist with making your stay enjoyable and worry free.

Guest favorite

Hotel room in Venice

4.86 out of 5 average rating, 205 reviews

Near Downtown/Beach | Tropical Villas Venice Beach

Tropical Villas of Venice Beach offers 10 Villas on the Island of Venice FL. The Villas give the Old time Florida vibe with a convenient location to the beach, stores and restaurants. - 3 blocks from the beach - 2 blocks from the downtown - Near the Legacy Bike trail - In front of the beautiful John N. Park (Picnic) - Tropical gardens & swimming pool - Smart TV : NFLX, DIS +, Hulu, Espn+ - BBQ and Bikes and beach gears provided - Shark teeth equipment - Farmer Market every Saturday

Guest favorite

Guest suite in Sarasota

4.93 out of 5 average rating, 307 reviews

Beach & Town Posh Location! Jungle Paradise Studio

PRIME Town/Beach 3.2 miles location! *Private Studio* Access Non shared Pool. Studio w/private entrance & private patio @Designers private Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Beach, shops, dining, & 5mins/Downtown Sarasota. Walk/local markets/ dining/movies & shopping New King bed. New 50" TV. Off street parking. No Smoking/Vaping! Wet Bar, No kitchen, lite meals only! No hotels in my exclusive area! Live like a local!

Guest favorite

Home in Nokomis

4.93 out of 5 average rating, 103 reviews

Family Oasis/Entire House/Heated Pool/Near Beach

Beautiful House with 3 bedrooms, heated pool, mini golf and two-car garage. Great location. five-minute drive to the beach. near shopping plazas, restaurants, and the famous Legacy Trail perfect for biking, running, and more. Situated at a dead-end in a peaceful community. Lots of outdoor space around the house with beautiful palm trees and a large patio. bicycles, board games, cornhole, a gas grill, and more at your disposal. Lots of places to visit in the Sarasota and Venice area.

Guest favorite

Home in Venice

4.91 out of 5 average rating, 177 reviews

Vacation Rental with private swimming pool

Located in a desirable community of South Venice. Venice, Manasota, Nokomis and Sharky’s beaches are located only 5 miles away. The historic Venice Avenue of unique shops, restaurants, special events. Farmer market, tennis courts, and children fountain are close by. Newly renovated home and swimming pool in a quiet peaceful area in an ideal place for any season gateway.A great place for biking, running and walking. My place great for couples, solo adventurers or families with kids.

Guest favorite

Home in Venice

4.92 out of 5 average rating, 124 reviews

Near historical downtown Venice and Venice beach

Two bedroom, 2 bath updated home in a quiet neighborhood, near Venice Beach. Privacy fence surrounds the backyard, palm trees line the front yard. Enjoy a screened in pool with a cup of coffee, relaxing on the patio, while, watching the squirrels play, blue jays and cardinals fly around the large Mango tree, and Magnolia tree, or end your busy day with a night swim under the stars with the outdoor night lights on. Either way, its a relaxing way of life near Venice beach!

Guest favorite

Rental unit in Sarasota

4.88 out of 5 average rating, 120 reviews

Little gem just 6 min from Siesta+heated pool

★ "Second floor 1 bedroom 1 bathroom apartment" ★ "An incredible apartment and 6 star hospitality!" • 6 min drive from Siesta • Shared heated pool just 200 feets • Screened lanai • pet friendly, no pet fee, no deposit • Fully stocked kitchen • 555 sqft home • walking distance Publix, restaurants, bars • 30 min. drive from SRQ Airport • 60 min. drive from Tampa Airport • 8 min. drive from I-75 • 20 min. drive from the downtown and St. Armand Circle

Guest favorite

Condo in Sarasota

4.9 out of 5 average rating, 138 reviews

Gateway to Siesta Key - 1/2 mile to the Beach!

Super comfy and newly updated 2 bedroom/2 bathroom fully-equipped condo that sleeps 4 - only 1/2 mile from the Gulf of Mexico! Located in a small and quiet complex with very convenient access to the beach as well as all of Sarasota's shopping and dining (without beach traffic). Our condo is exceptionally clean, well-kept and has all the comforts of home on your tropical getaway. Minimum age of primary renter is 25 years old. Proof of age required.

Guest favorite

Guest suite in Venice

4.93 out of 5 average rating, 179 reviews

Serene Suite/Tropical oasis

My place is a lovely, modest home that offers charm, comfort, QUIET. and privacy…convenient, quiet location ..six minutes by car to the nearest beach! Your suite is one whole side of the house . Great privacy! 3 rooms: bedroom with super comfortable queen bed....a sitting room with sofa, table, refrigerator/microwave/toaster oven/ coffeemaker...a full bath and access to a beautiful Lanai and sparkling (unheated)pool.

Superhost

Vacation home in Nokomis

4.82 out of 5 average rating, 61 reviews

"Sea Turtle" Saltwater Pool, Shore Beach House

The Sea Turtle cottage is one of 5 in this beautiful Resort. This is a private resort with a relaxing vibe and short walk to the beach. We have set up social distancing at the pool for safely. Speaking of sterilization, we are using UV-C Light in each unit after guests leave to make sure it is safe for us and our guests. We also have bikes for your use, beach chairs, and umbrellas.