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

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Our top choices for Osprey Village holiday 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
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 £138
includes taxes & fees
1 Sept - 2 Sept
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 £608
includes taxes & fees
4 Sept - 5 Sept
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, (5,815 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is £112
includes taxes & fees
2 Sept - 3 Sept
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 £258
includes taxes & fees
1 Sept - 2 Sept
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.
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 £260
includes taxes & fees
1 Sept - 2 Sept
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
9.0 out of 10, Wonderful, (81 reviews)
"Good"
United States
Gelsy
The price is £346
includes taxes & fees
1 Sept - 2 Sept
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, (76 reviews)
"Great short stay. Close walk to the beach! "
United States
Tera S.
The price is £339
includes taxes & fees
1 Sept - 2 Sept
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 £192
includes taxes & fees
1 Sept - 2 Sept
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 £160
includes taxes & fees
1 Sept - 2 Sept
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 £541
includes taxes & fees
6 Sept - 7 Sept
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 £192
includes taxes & fees
1 Sept - 2 Sept
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 £165
includes taxes & fees
1 Sept - 2 Sept
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, (2,433 reviews)
"This place was perfect!"
United States
Kat
The price is £95
includes taxes & fees
1 Sept - 2 Sept
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 £154
includes taxes & fees
1 Sept - 2 Sept
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 £292
includes taxes & fees
1 Sept - 2 Sept
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 £381
includes taxes & fees
1 Sept - 2 Sept
🌷 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 £311
includes taxes & fees
2 Sept - 3 Sept
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 £212
includes taxes & fees
1 Sept - 2 Sept
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

Everything you need to know about Osprey Village holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey Village holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey Village holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osprey Village holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey Village. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osprey Village holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osprey Village holiday rentals we have selected for you start as low as £79 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osprey Village rentals

At Expedia, we put the best Osprey Village holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Osprey Village rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey Village holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey Village. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Osprey Village?

Yes, there are holiday rentals close to the most popular sights in Osprey Village, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osprey Village has to offer?

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

How many holiday rentals will I find in Osprey Village?

Expedia has 3 holiday 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 Jim Neville Marine Preserve, 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 holiday rentals like in Osprey Village?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osprey Village. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.