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

Osprey Village Holiday Rentals

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Our top choices for Osprey Village holiday rentals

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,924 reviews)
"Amazing resort,"
United States
kurt
The price is NZ$315
includes taxes & fees
30 Sept - 1 Oct
Tropical Beach Resorts

2. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (386 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is NZ$366
includes taxes & fees
13 Oct - 14 Oct
Tiny House Siesta

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,311 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is NZ$341
includes taxes & fees
8 Oct - 9 Oct
Captiva Beach Resort

4. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,454 reviews)
"This place was perfect!"
United States
Kat
The price is NZ$244
includes taxes & fees
30 Sept - 1 Oct
Hibiscus Suites - Gateway to Siesta Key

5. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.4 out of 10, Exceptional, (81 reviews)
"The property was clean and had great decor! They provide everything you need for the beach and the pool is a great added bonus. Perfect location with being so close the restaurants and the beach. We are already planning our next stay!"
United States
Meghan
The price is NZ$567
includes taxes & fees
30 Sept - 1 Oct
Siesta Key Island Rentals

6. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (185 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is NZ$471
includes taxes & fees
13 Oct - 14 Oct
SeaSpray Resort

7. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (90 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is NZ$530
includes taxes & fees
11 Oct - 12 Oct
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

8. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Nice little property,very well kept.Host was very nice and helpful.Will be back again."
United States
Greg
The price is NZ$405
includes taxes & fees
30 Sept - 1 Oct
Casey Key Resort

9. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (685 reviews)
"Great stay!!"
United States
Genghis
The price is NZ$377
includes taxes & fees
30 Sept - 1 Oct
A Beach Retreat

10. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
The price is NZ$558
includes taxes & fees
4 Oct - 5 Oct
[lounge like locals] walk to siesta beach +bikes

11. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is NZ$546
includes taxes & fees
30 Sept - 1 Oct
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

12. 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 NZ$465
includes taxes & fees
1 Oct - 2 Oct
Siesta Key, Sea Horse Villa, Pool. Daily rentals

13. Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (77 reviews)
"Great stay"
United States
Allison H.
The price is NZ$677
includes taxes & fees
30 Sept - 1 Oct
Siesta Key Village-Suite #3: A Block to the Beach!

14. Dolphin Villa - Pool - Steps to Siesta Key Village

Dolphin Villa - Pool - Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is NZ$593
includes taxes & fees
30 Sept - 1 Oct
Dolphin Villa - Pool - Steps to Siesta Key Village

15. 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 NZ$581
includes taxes & fees
1 Oct - 2 Oct
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

16. Heart of Village: Dog-Friendly w/ Pool & Parking

Heart of Village: Dog-Friendly w/ Pool & Parking
Siesta Key Village
9.2 out of 10, Wonderful, (16 reviews)
"Love the place. Perfect location. Close to village, close to beach. Highly suggest and will definitely be back in the future. Host was very friendly and accommodating."
United States
Jeffrey B.
The price is NZ$611
includes taxes & fees
30 Sept - 1 Oct
Heart of Village: Dog-Friendly w/ Pool & Parking

17. 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 NZ$597
includes taxes & fees
1 Oct - 2 Oct
Bright & Beachy–Beach Club Siesta Key 100A by RVA

18. Tropical 🌴 private, 💯 walkable,⛱️ beach chairs n towels, W&D, park on property 🎾

Tropical 🌴 private, 💯 walkable,⛱️ beach chairs n towels, W&D, park on property 🎾
Central Sarasota
9.6 out of 10, Exceptional, (75 reviews)
"Place was very nice and welcoming we will be back !!!!"
United States
Sue R.
The price is NZ$659
includes taxes & fees
26 Oct - 27 Oct
Tropical 🌴 private, 💯 walkable,⛱️ beach chairs n towels, W&D, park on property 🎾

19. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (93 reviews)
"Loved the house. It had everything you could possibly need"
United States
Erin G.
The price is NZ$1,096
includes taxes & fees
3 Oct - 4 Oct
Oceanfront home

20. Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
South Village
8.8 out of 10, Excellent, (89 reviews)
"Great location and easy access to the beach."
United States
Erica B.
The price is NZ$592
includes taxes & fees
30 Sept - 1 Oct
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Osprey Village holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Osprey Village. 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 Osprey Village. 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 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 holiday 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 Osprey Village short-term rentals, that won’t be hard to do.

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?

Tropical Villas of Venice Beach: This holiday home rental outside of Osprey Village is located near the beach, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Make the most of garden in this rental home to help you unwind.

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 Mote Marine Laboratory & Aquarium, or get outside and enjoy nature at Siesta Key Beach. Lido Beach and Turtle Beach are a couple of places you'll find in the wider 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.