A marina with docked boats, a wooden bridge, and a building with a red roof.

Osprey Village Vacation Rentals

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Our top choices for Osprey Village vacation rentals

1. Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Siesta Key
9.4 out of 10, Exceptional, (99 reviews)
"Great location"
United States
Daphane
The price is CA $317
CA $540 total
includes taxes & fees
Sep 1 - Sep 2
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

2. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,302 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
The price is CA $208
CA $259 total
includes taxes & fees
Sep 3 - Sep 4
Captiva Beach Resort

3. Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout
South Village
9.8 out of 10, Exceptional, (97 reviews)
"It was all great, really enjoyed our stay."
United States
Roger K.
The price is CA $442
CA $1,201 total
includes taxes & fees
Sep 4 - Sep 5
Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

4. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,797 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is CA $176
CA $235 total
includes taxes & fees
Aug 30 - Aug 31
Tropical Beach Resorts

5. Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (119 reviews)
"The pool and proximity to the beach are great "
United States
Evan C.
The price is CA $222
CA $477 total
includes taxes & fees
Aug 29 - Aug 30
Bright & Beachy–Beach Club Siesta Key 100A by RVA

6. Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
South Village
9.0 out of 10, Wonderful, (77 reviews)
"We found this property to be delightful. We loved the balcony for enjoying our evenings. I would have liked to see a table on the balcony for eating at, it is FL, and I wanted to sit outside for my meals. It was a very close walk to the beach, the pool and hot tub were in excellent working condition. We enjoyed the property. We had a problem, but they had maintenance there within an hour to fix it, I call that a win for the property. "
United States
Jackie J.
The price is CA $278
CA $659 total
includes taxes & fees
Aug 29 - Aug 30
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

7. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (105 reviews)
"Great birthday weekend. Awesome location to the beach and nightlife. Highly recommend."
United States
Cindy F.
The price is CA $223
CA $479 total
includes taxes & fees
Aug 29 - Aug 30
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

8. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
8.8 out of 10, Excellent, (80 reviews)
"Beautiful place"
United States
Chad
The price is CA $276
CA $653 total
includes taxes & fees
Sep 1 - Sep 2
2BR Beach Style w Pool Beach Club Siesta 204C RVA

9. 2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA

2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA
South Village
9.2 out of 10, Wonderful, (75 reviews)
"Great short stay. Close walk to the beach! "
United States
Tera S.
The price is CA $260
CA $635 total
includes taxes & fees
Aug 29 - Aug 30
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA

10. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
The price is CA $133
CA $351 total
includes taxes & fees
Aug 31 - Sep 1
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

11. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
South Village
9.8 out of 10, Exceptional, (34 reviews)
"Great stay."
United States
James J.
The price is CA $148
CA $314 total
includes taxes & fees
Sep 27 - Sep 28
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

12. Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
South Village
9.6 out of 10, Exceptional, (72 reviews)
"It was very clean and close to the beach. Perfect location."
United States
Cortney
The price is CA $447
CA $1,020 total
includes taxes & fees
Aug 31 - Sep 1
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

13. Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (54 reviews)
"Perfect weekend getaway stay for my husband and I! The cottage had everything we needed, was thoroughly cleaned and location was perfect for restaurant hopping and beach going. Would definitely stay again!"
United States
Allie A.
The price is CA $133
CA $351 total
includes taxes & fees
Sep 1 - Sep 2
Siesta Key, Sea Horse Villa, Pool. Daily rentals

14. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (384 reviews)
"Great place"
United States
Mario
The price is CA $117
CA $320 total
includes taxes & fees
Sep 11 - Sep 12
Tiny House Siesta

15. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,429 reviews)
"This place was perfect!"
United States
Kat
The price is CA $155
CA $175 total
includes taxes & fees
Aug 31 - Sep 1
Hibiscus Suites - Gateway to Siesta Key

16. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (671 reviews)
"Lovely place on a family beach."
United States
Robert
The price is CA $255
CA $288 total
includes taxes & fees
Sep 23 - Sep 24
A Beach Retreat

17. Jetties Pointe Cottage #5 - 408 “Casey Key”

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (33 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
The price is CA $214
CA $535 total
includes taxes & fees
Aug 30 - Aug 31
Jetties Pointe Cottage #5 - 408 “Casey Key”

18. 🌷 Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach

🌷 Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach
Siesta Key
9.4 out of 10, Exceptional, (103 reviews)
"This was my second time going to Vanessa’s place and I love it. The place has a perfect location, just across the street from the beautiful siesta key beach. The place is very clean and it has everything you need for a perfect vacation. Vanessa is very friendly and quick to respond via phone or message. I will definitely going back and strongly recommended to anyone who is looking for a perfect beach vacation"
United States
Eglantina T.
The price is CA $353
CA $720 total
includes taxes & fees
Sep 1 - Sep 2
🌷 Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach

19. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (190 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is CA $300
CA $593 total
includes taxes & fees
Sep 2 - Sep 3
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

20. Studio Retreat Across the Street from Beautiful Siesta Key Beach

Studio Retreat Across the Street from Beautiful Siesta Key Beach
Siesta Key
9.0 out of 10, Wonderful, (167 reviews)
"It was a great place. And just about a 5 min walk to the beach. "
United States
DESIREE
The price is CA $229
CA $403 total
includes taxes & fees
Sep 1 - Sep 2
Studio Retreat Across the Street from Beautiful Siesta Key Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osprey Village Hotel Reviews

Find out more about Osprey Village

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osprey Village. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Osprey Village?

Yes, we give you a choice of vacation rentals in Osprey Village close to Nancy's Consignments, or you can go with a more remote option if you're looking for extra privacy while you relax.

What's the top vacation rental that Osprey Village has to offer?

Siesta Key Island Rentals: This vacation home rental near Osprey Village comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals will I find in Osprey Village?

Expedia has 3 vacation rentals for your stay in Osprey Village.

What can I see and do in Osprey Village?

While exploring the area, visit family-friendly sights like Nancy's Consignments, or get outside and enjoy nature at Siesta Key Beach. Venice Beach and Lido Beach are other popular places to visit in the area.

What are vacation rentals like in Osprey Village?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Osprey Village. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.