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.

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Guest favorite

Villa in Nokomis

4.92 out of 5 average rating, 142 reviews

*NEW MAY Avail! 5* Family BEACH Villa 2KING/2BTH*

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...:)

Aug 25 – Sep 1

G$35,621 GYD per night

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 477 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

Oct 28 – Nov 4

G$29,451 GYD per night

Guest favorite

Apartment in Sarasota

4.88 out of 5 average rating, 138 reviews

Pets friendly modern studio 5 mi to Siesta Key

Renovated Studio/1 full bath apartment in a duplex house with separate entrance in a quiet and secure neighborhood. 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.

Jun 2 – 9

G$22,287 GYD per night

Guest favorite

Guesthouse in Sarasota

4.96 out of 5 average rating, 248 reviews

Sarasota guest house only 8 miles to Siesta Key

Our Florida-themed guest house has everything you need to enjoy your vacation in beautiful Sarasota, Florida. It is a very comfortable, clean and private one bedroom and one bathroom guest house. It is a completely separate space and has it's own private entrance. It is conveniently located in a quiet, safe neighborhood near Interstate I-75, Shopping, Dining, Twin Lakes Park, Serenoa Golf Course, Myakka River State Park and just 8 miles from the #1 beach in the U.S. - Siesta Key Beach.

Aug 10 – 17

G$20,807 GYD per night

Guest favorite

Apartment in Nokomis

4.88 out of 5 average rating, 169 reviews

Casa del Sol I (Non-Smoking Property)

A four minute walk and your toes are in the sand on the beach of beautiful Nokomis Beach on the Gulf of Mexico! This quiet, comfy one bedroom apartment with a sunset deck is on the second floor over your private 2 car carport. Newly remodeled with 49” TV with AppleTV you can sleep 2 additional guests on a comfortable queen size air bed which automatically opens up and closes at a touch of a button. Shopping, banking and post office 1 mile away and 10 restaurants a few minutes away.

Oct 2 – 9

G$22,811 GYD per night

Guest favorite

Home in Sarasota

4.99 out of 5 average rating, 201 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Close to restaurants and shopping. 1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. (URL HIDDEN) Linens & towels are all new. New tile and wood floors throughout. Quite neighborhood for walking .

Apr 22 – 29

G$23,940 GYD per night

Guest favorite

Apartment in Sarasota

5.0 out of 5 average rating, 117 reviews

New Apartment In a Private House Near Siesta

Large brand new construction 900 square foot 1 bedroom apartment. Beautifully furnished, efficient apartment attached to the side of the main house. This unit has a private entrance with bright, modern interior. The apartment offers 2 queen size beds. The full bathroom has a large shower. A Washer and dryer located inside the apartment. Nestled on a quiet street with easy access to Siesta key. Located 1 mile from the Stickney Point bridge with easy access to Siesta Key. Great location!

Oct 19 – 26

G$29,062 GYD per night

Guest favorite

Guest suite in Sarasota

4.91 out of 5 average rating, 273 reviews

Siesta Keys stylish and affordable Airbnb.

Relax while you stay in a colorful and warm Siesta Key/Sarasota neighborhood home that is only minutes from the famous Siesta Key beach. Enjoy your private, safe, and comfortable suite while being in close reach to all that Florida has to offer. Your suite is spacious and accommodating, wether your an individual, couple, family, or group of friends we have the space and amenities for you to maximize both your comfort and fun time while here in Florida :-)

Nov 3 – 10

G$20,498 GYD per night

Guest favorite

Cottage in Nokomis

4.98 out of 5 average rating, 123 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Bella Vita! (The Good Life!)…that feeling when you wake up each day in this little slice of Paradise. This is the spot to enjoy a warm peaceful getaway from the rest of the world...just arrive with your bathing suit/flip flops and walk 1.5 blocks to the warm Gulf waters. Tranquillity of beach life, beautiful sunsets and lazy days of fishing and bird watching. Visit the Jetties, where you can see dolphins, manatees and rays, is only 1/2 mile away.

Aug 11 – 18

G$24,973 GYD per night

Guest favorite

Bungalow in Osprey

4.78 out of 5 average rating, 320 reviews

Osprey,Buttonwood Cottage.Hot tub -patio.Sublime !

Floridian Tiny Cottage! Buttonwood Cottage is wonderfully located central to the downtowns and beaches of Sarasota and Venice with a private patio space and hot tub. 15 minutes away for the number 1 beach in USA "Siesta Key" . You'll feel that you stepped back in time upon arrival to our charming homestead. I follow Airbnb’s enhanced cleaning protocol, which was developed with expert guidance. Here are a few highlights:

Feb 9 – 16

G$26,643 GYD per night

Guest favorite

Guest suite in Sarasota

4.97 out of 5 average rating, 350 reviews

Adorable studio close to Siesta beach!

Come stay in this private studio with its own fenced in patio in the back! Has shared washer and dryer. New Queen bed ,pullout couch (twin). gas grill,toaster oven/airfryer, microwave , hot plate for cooking and full fridge plus ac unit. Rainfall showerhead and river stones on shower floor. beach chairs ,towels available. Off street parking in driveway. The famous, huge fresh market " Detweilers" is only 1.5 miles away

Oct 8 – 15

G$19,196 GYD per night

Guest favorite

Cottage in Sarasota

4.9 out of 5 average rating, 175 reviews

"Honeybee Hideaway" Cozy Cottage Near SIESTA KEY

Experience the Honeybee cottage, a classic coastal retreat in historic Sarasota, minutes from Siesta key Beach. Enjoy, cozy vibes, modern amenities, fast, Wi-Fi, and shared laundry facilities. Embrace, tranquility and convenience in this charming oasis, combining rich history, with world-class beaches for a memorable getaway.

Aug 2 – 9

G$24,158 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Osprey vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

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

4.94 out of 5 average rating, 138 reviews

Sea-esta Cottage-cheerful 2bd/1ba w/ free parking

Sep 4 – 11

G$23,757 GYD per night

Superhost

Guest suite in Venice

4.86 out of 5 average rating, 103 reviews

Adorable-Guestsuite for 2 near beautiful beaches

Nov 12 – 19

G$22,726 GYD per night

Guest favorite

Guest suite in Sarasota

4.97 out of 5 average rating, 116 reviews

Private & Luxurious studio. “The Beach house”

Jul 18 – 25

G$19,564 GYD per night

Guest favorite

Guesthouse in Sarasota

4.86 out of 5 average rating, 371 reviews

The Cottage, very close to Siesta Beach!

Dec 2 – 9

G$23,877 GYD per night

Guest favorite

Cottage in Osprey

4.96 out of 5 average rating, 23 reviews

Mattie’s Cottage by the Bay

Jun 20 – 27

G$20,896 GYD per night

Guest favorite

Apartment in Nokomis

4.99 out of 5 average rating, 68 reviews

Charming 1 bedroom apartment for 2 with pool.

May 30 – Jun 6

G$26,249 GYD per night

Guest favorite

Home in Osprey

4.91 out of 5 average rating, 33 reviews

Sand Dollar Cottage - 15m to Siesta / Casey Key

Sep 30 – Oct 7

G$33,618 GYD per night

Guest favorite

Home in Nokomis

5.0 out of 5 average rating, 9 reviews

Updated house close to the Beach

May 7 – 14

G$20,458 GYD per night

Show all

Other great vacation rentals in Osprey

Guest favorite

Home in Nokomis

4.9 out of 5 average rating, 40 reviews

Cheerful, sparkling 2 bedroom cottage, 1.8 miles from beach

Aug 18 – 25

G$19,269 GYD per night

Guest favorite

Guest suite in Venice

4.98 out of 5 average rating, 55 reviews

Venice Beach Studio

Aug 12 – 19

G$15,297 GYD per night

Guest favorite

Vacation home in Nokomis

4.94 out of 5 average rating, 32 reviews

The "Seahorse" Peaceful Sunshine & Saltwater

Jul 26 – Aug 2

G$26,773 GYD per night

Guest favorite

Cottage in Nokomis

4.92 out of 5 average rating, 84 reviews

The "Turtle Cottage" - a charming beachy retreat.

Nov 24 – Dec 1

G$27,610 GYD per night

Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 25 reviews

Beach house #2

Aug 9 – 16

G$21,537 GYD per night

Guest favorite

Condo in Sarasota

4.98 out of 5 average rating, 59 reviews

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Sep 20 – 27

G$34,973 GYD per night

Guest favorite

Home in Nokomis

5.0 out of 5 average rating, 46 reviews

Charming vacation home, short walk to the beach

Jul 22 – 29

G$33,246 GYD per night

Guest favorite

Home in Sarasota

5.0 out of 5 average rating, 29 reviews

Siesta Key Fully-Renovated Unit 5 min to the beach

Aug 20 – 27

G$23,893 GYD per night

Show all

Quick stats about vacation rentals in Osprey

Total rentals
80 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
G$12,546 GYD 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 50 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 30 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 60 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 house rentals in Osprey?
Experience the best of Osprey with our house 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 condo rentals in Osprey have wifi?
Absolutely! We offer over 10 condo 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.

Osprey vacation rentals

Top-rated vacation rentals in Osprey

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Osprey vacation rentals

Stay near Osprey's top sights

Other great vacation rentals in Osprey

Cottage in Sarasota

Guest suite in Venice

Guest suite in Sarasota

Guesthouse in Sarasota

Cottage in Osprey

Apartment in Nokomis

Home in Osprey

Home in Nokomis

Other great vacation rentals in Osprey

Home in Nokomis

Guest suite in Venice

Vacation home in Nokomis

Cottage in Nokomis

Home in Sarasota

Condo in Sarasota

Home in Nokomis

Home in Sarasota

Quick stats about vacation rentals in Osprey

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Osprey?

Are there pet-friendly vacation rentals in Osprey?

Are there Osprey vacation rentals on Airbnb with pools?

Do condo rentals in Osprey have a gym?

Are there family-friendly house rentals in Osprey?

How much does it cost to stay in house rentals in Osprey?

Do condo rentals in Osprey have wifi?

Do condo rentals in Osprey have air conditioning?

Do house rentals in Osprey have a bbq area?

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

Destinations to explore