Vacation rentals with a pool in Osprey

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Osprey

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

*NEW May 17 CX 30% OFF! Sarasota #1 Luxury Villa*

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Nov 13 – 20

G$131,439 GYD per night

Guest favorite

Apartment in Sarasota

4.96 out of 5 average rating, 207 reviews

Private 2 Bedroom Suite with Kitchenette

A lovely private suite, attached to our home, consisting of 2 bedrooms, bath, and kitchenette/dining area. Features a private entrance and use of our family pool, lanai & sauna. Located close to I75, and minutes away from Nathan Benderson Park, and the Mall at University Town Center where you'll find many shopping & eating options. You will also be only 12 miles from the beautiful white sand beach of Siesta Key with all of the activities it affords. Located in a family friendly neighborhood.

Jun 15 – 20

G$27,748 GYD per night

Guest favorite

Home in Sarasota

4.94 out of 5 average rating, 297 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.

Jul 19 – 26

G$58,875 GYD per night

Guest favorite

Condo in Venice

4.87 out of 5 average rating, 141 reviews

The Studio at the Beach 56

This is a studio first floor apartment, only 50 feet from the oversize pool and approximately 300 steps to the beach! Quick bike ride or a 20 to 25 minute walk to all of downtown Venice has to offer. About the same to Sharkeys and the fishing pier. Inside you will find all you would expect from a very nicely appointed studio. Efficiency kitchen new appliances and everything you need to prepare a simple meal. Lots of pillows super comfy brand new queen bed will ensure a restful nights sleep.

Oct 13 – 20

G$26,491 GYD per night

Guest favorite

Guesthouse in Englewood

4.97 out of 5 average rating, 205 reviews

Shabby chic cottage with pool one mile from beach

This adorable shabby chic decor style studio cottage for 2 is located on one acre of old Florida landscaping. Great area for walking, biking, for exercise. Included with this home is access to a pool and large, lovely lanai, just outside the door. Head south for 7 min to historic Dearborn St or north for 3 miles to Venice. This location offers peace and tranquility combined with accessibility to endless activities nearby. 2 twins OR one King, per your preference. The pool is unheated.

May 18 – 23

G$23,973 GYD per night

Guest favorite

Hotel room in Venice

4.88 out of 5 average rating, 177 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

Oct 27 – Nov 3

G$30,677 GYD per night

Guest favorite

Home in Venice

4.9 out of 5 average rating, 162 reviews

Venice Pool Villa with Bikes Kayaks Great Beaches!

Relaxing pool home with 2 bedrooms, 1 king bed, 1 queen bed, 1 sofa double bed and one single foldout bed. 2 bathroom pool home just a 8 minute ride away from Manasota beach. Venice beach and caspersons beaches close by too. A great selection of restaurants and plenty of shopping and convenient grocery stores just 5 minutes away!. Also close to bike trails with two FREE bikes at the house and FREE kayaks too. My home is great for everyone! Pets welcome with pet fee, large fenced yard!

Dec 7 – 14

G$31,921 GYD per night

Guest favorite

Condo in Venice

4.82 out of 5 average rating, 219 reviews

Updated beachy condo - ready for you!

Conveniently located on Venice Island. This recently renovated, cozy, light an bright beachside condo has everything you need for your vacation. We have beach chairs, umbrella, towels and cooler. The efficiency unit has a full size frige, stovetop, microwave and convection oven. Comfy queen bed, Xfinity cable TV & Wifi in the condo. Park right in front of your unit, 1st floor - no stairs! Kayak rentals at the beach, bike rentals nearby. Bring your flip flops and sun tan lotion!

Dec 12 – 19

G$27,639 GYD per night

Guest favorite

Home in Venice

4.91 out of 5 average rating, 116 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!

May 24 – 31

G$40,495 GYD per night

Guest favorite

Guesthouse in Sarasota

4.89 out of 5 average rating, 168 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

Come and enjoy our newly remodeled 400 square foot laid back beached themed guest house. Located just 1.5 miles away from Sarasota/ Bradenton airport, and less than 10 miles away from our world famous beaches. Whether you are a single person in search of a long term stay or a family looking for a short vacation, we have the place for you. Our guest area is attached to our main residence and has a private entrance. Enjoy our shared swimming pool and outside patio areas.

Nov 12 – 19

G$21,914 GYD per night

Guest favorite

Home in Venice

4.89 out of 5 average rating, 184 reviews

Perfect vacation home 3 miles from beach.

. Located in a desirable community of Venice Garden. Several beautiful beaches such as Venice, Manasota and Sharky's are located only few miles away. This ideal vacation home with swimming pool sits in a quite, peaceful area making it an ideal place for any season gateway. This is a great place for biking, running and walking. You will love my home because it can accommodate couples, solo adventures, or families with kids. There is no BBQ on the property.

Oct 27 – Nov 3

G$32,460 GYD per night

Guest favorite

Guesthouse in Sarasota

4.99 out of 5 average rating, 131 reviews

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

Aug 15 – 22

G$27,681 GYD per night