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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.

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Condo in Sarasota

4.8 out of 5 average rating, 199 reviews

Near beach. Pool view. King bed. Daily rentals

The ‘pool view’ overlooks the swimming pool & has a private covered porch for shade 1 bed 1 bath w/ private entrance. The bedroom has a king sized Tempurpedic mattress bed. The living room has a kitchenette area with a fridge, freezer, microwave, coffee maker and the essentials. There is a HD smart TV with cable and apps. Separate bedroom with King size Tempurpedic bed 3 mins walk to Crescent beach access You can walk to a great choice of places to eat and drink Max 2 guests No smoking, pets

Jan. 9 – 16

$165 CAD per night

Guest favourite

Island in Sarasota

4.97 out of 5 average rating, 301 reviews

NEW MAY CX! last min SALE Sarasota #1 Luxury!

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. 5 – 12

$997 CAD per night

Guest favourite

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. 14 – 19

$224 CAD per night

Guest favourite

Condo in Venice

4.83 out of 5 average rating, 174 reviews

Venice Beach Studio 71

This is a studio second floor apartment, only 50’ from the oversized pool and approximately 300 steps to the beach! Quick bike ride, or 20-25 min walk to all of what downtown Venice has to offer. About the same to Sharky’s and 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 simple meals. Lots of pillows and a super comfy brand new queen bed will ensure a restful night’s sleep.

Aug. 19 – 26

$212 CAD per night

Guest favourite

Home in Sarasota

4.94 out of 5 average rating, 296 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.

Aug. 2 – 9

$396 CAD per night

Guest favourite

Guesthouse in Englewood

4.97 out of 5 average rating, 202 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.

Apr. 16 – 23

$214 CAD per night

Guest favourite

Hotel room in Venice

4.88 out of 5 average rating, 175 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

Aug. 6 – 13

$227 CAD per night

Guest favourite

Home in Venice

4.89 out of 5 average rating, 161 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!

Sep. 21 – 28

$267 CAD per night

Guest favourite

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

$218 CAD per night

Guest favourite

Guesthouse in Sarasota

5.0 out of 5 average rating, 100 reviews

Magical Guesthouse 1 mi from SRQ airport

Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Sep. 22 – 29

$213 CAD per night

Guest favourite

Home in Venice

4.91 out of 5 average rating, 115 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!

Sep. 12 – 19

$330 CAD per night

Guest favourite

Home in Venice

4.88 out of 5 average rating, 182 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

$265 CAD per night

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House rentals with a pool

Guest favourite

Home in Sarasota

4.81 out of 5 average rating, 107 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

Sep. 26 – Oct. 3

$283 CAD per night

Home in Venice

4.85 out of 5 average rating, 136 reviews

Getaway Relax Home/Beaches 5-10minutes/Heated Pool

Jun. 26 – Jul. 3

$232 CAD per night

Guest favourite

Home in Sarasota

4.97 out of 5 average rating, 206 reviews

Your private retreat near Siesta Key Beach.

Apr. 15 – 22

$714 CAD per night

Guest favourite

Home in Sarasota

4.93 out of 5 average rating, 106 reviews

Lake Front House with a Pool

Aug. 26 – Sep. 2

$389 CAD per night

Guest favourite

Home in Osprey

5.0 out of 5 average rating, 23 reviews

Heated Pool | 3 Beds | Near Beaches and parks

Sep. 8 – 15

$385 CAD per night

Guest favourite

Home in Nokomis

4.96 out of 5 average rating, 27 reviews

Tropical Pool Paradise - Minutes from the Beach!

Oct. 29 – Nov. 5

$458 CAD per night

Guest favourite

Home in Nokomis

4.95 out of 5 average rating, 19 reviews

Blue Sky Retreat

May 6 – 13

$397 CAD per night

Home in Nokomis

5.0 out of 5 average rating, 5 reviews

Sandy Beaches Minutes Away! Fun in the sun Resort

Jun. 21 – 28

$189 CAD per night

Condo rentals with a pool

Guest favourite

Condo in Sarasota

4.89 out of 5 average rating, 127 reviews

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

May 28 – Jun. 4

$244 CAD per night

Guest favourite

Condo in Sarasota

4.95 out of 5 average rating, 187 reviews

Newly Renovated + Washer/Dryer- Walk everywhere!

Sep. 11 – 18

$294 CAD per night

Guest favourite

Condo in Bradenton

4.94 out of 5 average rating, 108 reviews

Newly remodeled cozy 2 bed/2.5 bath townhome

Sep. 19 – 26

$247 CAD per night

Guest favourite

Condo in Sarasota

4.92 out of 5 average rating, 122 reviews

Beachside Siesta Key Cottage steps from the ocean

May 28 – Jun. 2

$479 CAD per night

Guest favourite

Condo in Siesta Key

4.96 out of 5 average rating, 275 reviews

On the Beach; Siesta Key SunBum Studio

Jan. 11 – 18

$729 CAD per night

Guest favourite

Condo in Sarasota

4.95 out of 5 average rating, 123 reviews

Cozy Beach Side 1BD/2BA, Walk to Beach & Pool

Sep. 13 – 20

$337 CAD per night

Guest favourite

Condo in Nokomis

4.83 out of 5 average rating, 140 reviews

Private Beachside Kitchenette

Jul. 7 – 14

$542 CAD per night

Guest favourite

Condo in Siesta Key

4.85 out of 5 average rating, 131 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

Aug. 21 – 28

$257 CAD per night

Quick stats about vacation rentals with a pool in Osprey

Total rentals
60 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
390 reviews
Nightly prices starting at
$82 CAD before taxes and fees

Destinations to explore