Osprey vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Osprey

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Superhost

Villa in Nokomis

4.91 out of 5 average rating, 138 reviews

APR SALE! Sarasota Family BEACH Villa 2KING BR/2BA

EXCLUSVE CASEY KEY beach just .5 mi. away!! Sarasota 10 mins away! Miles of uncrowded beach! Two KING bedrooms, two bath villa! The Villa is a short 1 minute drive from Casey Key Beach! Two new 55" 4K T.V's. New appliances and furnishings throughout! Kayaking, biking, boating... all right here! Lush tropical backyard and fire pit. There are many wonderful restaurants and shops within a five minute drive. Restoring this Villa has been a labor of love for us, read our reviews!! Come stay...:)

Jun 16 – 23

$142 per night
Guest favorite

Apartment in Sarasota

4.88 out of 5 average rating, 132 reviews

Pets friendly modern studio 5 mi to Siesta Key

Renovated Studio/1 full bath apartment in a duplex house with separate entrance. Located in a West of "The Trail" in Southern Central Sarasota. Ideally close to Siesta Key, Turtle, Osprey and Nokomis beaches. Bike Routes throughout and short drive to downtown Sarasota, Osprey, Venice and wonderful amenities of Sarasota Lifestyle. Walking distance to restaurants, Selby aquatic center, Vamo Sarasota Bay Park, Westfield Mall, Total Wine, Costco, Target and CVS. Great, quiet and secure neighborhood.

Jan 2 – 9

$109 per night
Guest favorite

Home in Sarasota

4.91 out of 5 average rating, 142 reviews

Sunshine Suite, Minutes to Beach,Tropical Paradise

The Sunshine Suite.Lots of natural light in this totally updated modern 3 bed/1 bath home.It is a completely separate dwelling w separate entry from the other dwelling on the property sharing no common walls. Smart thermostat & door lock. Keyless entry.Brand new AC, gas oven, quartz counter w/ custom marble backsplash, modern & comfortable furniture, private outdoor area, gas BBQ grill, off street parking.Great location! Minutes to Siesta Key beach, shopping/UTC, interstate, hospital & downtown

Nov 3 – 10

$84 per night

Popular amenities for Osprey vacation rentals

Stay near Osprey's top sights

Walmart Supercenter14 locals recommend
Casey Key Fish House66 locals recommend
Evies @ Spanish Point17 locals recommend
Mad Moe's Sports Pub & Grill12 locals recommend
Max's Table15 locals recommend
Tervis Store4 locals recommend

Other great vacation rentals in Osprey

Guest favorite

Cottage in Sarasota

4.9 out of 5 average rating, 171 reviews

"Honeybee Hideaway" Cozy Cottage Near SIESTA KEY

Nov 5 – 12

$100 per night
Guest favorite

Guest suite in Sarasota

4.95 out of 5 average rating, 112 reviews

Sweet Siesta Suite

Aug 19 – 26

$94 per night
Guest favorite

Guest suite in Sarasota

4.91 out of 5 average rating, 265 reviews

Siesta Keys stylish and affordable Airbnb.

Oct 15 – 22

$85 per night
Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 127 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Jul 19 – 26

$111 per night
Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 254 reviews

Two Miles to Siesta Key

May 19 – 26

$119 per night
Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 196 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Oct 15 – 22

$99 per night
Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 238 reviews

Lovely guest house

Jul 22 – 29

$75 per night
Guest favorite

Condo in Venice

4.86 out of 5 average rating, 133 reviews

The Studio at the Beach 56

Dec 15 – 22

$110 per night
Guest favorite

Home in Sarasota

4.87 out of 5 average rating, 201 reviews

The Pineapple Suite.Teal tropical home in Sarasota

May 9 – 16

$84 per night
Guest favorite

Guesthouse in Sarasota

4.91 out of 5 average rating, 136 reviews

Cozy Guesthouse in central Sarasota!

Nov 22 – 29

$70 per night
Guest favorite

Cottage in Osprey

4.95 out of 5 average rating, 19 reviews

Mattie’s Cottage by the Bay

Jun 18 – 25

$86 per night
Guest favorite

Condo in Nokomis

5.0 out of 5 average rating, 13 reviews

Private Studio (entire space)

Aug 16 – 23

$81 per night

Other great vacation rentals in Osprey

Guest favorite

Home in Osprey

4.98 out of 5 average rating, 41 reviews

Bayview House - Osprey - 1 block to Bay!

Aug 2 – 9

$143 per night
Guest favorite

Cottage in Nokomis

4.91 out of 5 average rating, 82 reviews

The "Turtle Cottage" - a charming beachy retreat.

Dec 5 – 12

$113 per night
Superhost

Apartment in Nokomis

5.0 out of 5 average rating, 4 reviews

Condo a minute from the beach.

Jun 23 – 30

$108 per night
Guest favorite

Condo in Sarasota

5.0 out of 5 average rating, 36 reviews

Peaceful Glamorous 2 Bed Resort

Jun 15 – 22

$122 per night
Superhost

Home in Venice

4.79 out of 5 average rating, 81 reviews

PERFECT FLORIDA GETAWAY !

Apr 9 – 16

$99 per night
Guest favorite

Home in Nokomis

4.89 out of 5 average rating, 37 reviews

Cheerful, sparkling 2 bedroom cottage, 1.8 miles from beach

Jul 26 – Aug 2

$79 per night
Guest favorite

Guesthouse in Sarasota

5.0 out of 5 average rating, 26 reviews

The Cottage (In the Country) Cozy, Quiet Retreat

May 28 – Jun 4

$90 per night
Guest favorite

Guesthouse in Sarasota

4.92 out of 5 average rating, 66 reviews

Storybook Cottage With Pool Near the Bay & Beach

Jul 17 – 24

$117 per night
Guest favorite

Home in Nokomis

5.0 out of 5 average rating, 42 reviews

Charming vacation home, short walk to the beach

Jul 22 – 29

$125 per night
Guest favorite

Home in Sarasota

4.91 out of 5 average rating, 55 reviews

Sarasota Summer Beach Bliss!

Oct 2 – 9

$122 per night
Guest favorite

Guest suite in Venice

4.98 out of 5 average rating, 43 reviews

Venice Beach Studio

Jul 30 – Aug 6

$75 per night
Guest favorite

Home in Osprey

5.0 out of 5 average rating, 20 reviews

Private Oasis | Heated Pool | 3 Bed | Near Beaches

Sep 7 – 14

$329 per night

Quick stats about vacation rentals in Osprey

Total rentals

80 properties

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

50 properties are a good fit for families

Total number of reviews

1.5K reviews

Nightly prices starting at

$60 before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Osprey?

    Yes! Work meets play with ease at over 40 vacation rentals in Osprey featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Osprey?

    Four-legged friends are welcome in Osprey. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there Osprey vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Osprey, available on Airbnb. Make a splash and soak up the sun in style!

  • Do condo rentals in Osprey have a gym?

    Absolutely! We offer over 10 condo rentals with a gym in Osprey. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Osprey?

    Osprey has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Osprey?

    Experience the best of Osprey with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Osprey have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Osprey. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Osprey have air conditioning?

    Absolutely! We offer over 10 condo rentals with air conditioning in Osprey. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Osprey have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Osprey. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Osprey?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Osprey