Holiday Rentals Osprey Village from ฿2,037: Find Short-Term Rentals & Holiday Accommodations

Q: 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.

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Our top choices for Osprey Village holiday rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

South Village

Christine

฿6,351 total

includes taxes & fees

10 Nov - 11 Nov

An outdoor patio with a grill, white chairs, and a red umbrella.

2. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

฿5,650 total

includes taxes & fees

10 Nov - 11 Nov

A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

3. A Beach Retreat

Casey Key

Robin

฿6,989 total

includes taxes & fees

6 Dec - 7 Dec

An outdoor dining area with clear plastic chairs and tables, surrounded by greenery and a building in the background.

4. Captiva Beach Resort

South Village

Andriy

฿6,408 total

includes taxes & fees

10 Nov - 11 Nov

A modern living room with a sofa, a dining area, and a kitchen area.

5. Casey Key Resort

Casey Key

Jamie

฿8,051 total

includes taxes & fees

10 Dec - 11 Dec

A bedroom with a view of a swimming pool and outdoor seating.

6. SeaSpray Resort

Siesta Key

Geraldine

฿8,500 total

includes taxes & fees

11 Nov - 12 Nov

A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

7. Siesta Heron Suites & Villas

Siesta Key

Christopher Robert

฿10,305 total

includes taxes & fees

10 Nov - 11 Nov

A compact living space with a sofa, a television, a ceiling fan, and a door.

8. Tiny House Siesta

Sarasota

Staci

฿6,828 total

includes taxes & fees

22 Nov - 23 Nov

A pathway lined with directional signs leading to various amenities such as a pet area, bike trail, and beach.

9. Kon Tiki Inn

Venice Island

Joseph

฿6,166 total

includes taxes & fees

10 Nov - 11 Nov

A cozy living room with a stone fireplace, a flat-screen TV, a sofa, a coffee table, and a dining area with chairs.

10. The Inn On Siesta Key

Siesta Key

"Thank you Paige & Gabe! My husband & I had a wonderful stay last week in The Nook at your beautiful Inn. Absolutely loved the old Florida charm and perfect location. Your Inn is immaculately kept as well as comfortable. We especially loved our private patio with the fire pit at The Nook. The location of The Inn could not be more perfect being less than a 5 minute walk across the street to Siesta Key beach as well as a short 10 minute walk to town with all the restaurants & shops. Thanks again...

Karen Jean

฿10,762 total

includes taxes & fees

10 Nov - 11 Nov

A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a ceiling fan.

11. 4 Mi to Siesta Key Beach: Condo w/ Pool Access

Sarasota

Lori

฿10,099 total

includes taxes & fees

10 Nov - 11 Nov

An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

12. Beach Tree Cottage,Walk To Beach& Siesta

Siesta Key Village

A hot tub surrounded by a wooden fence, with lounge chairs and an umbrella in the background.

13. Yellow Palm Cottage, Heart of Siesta Key

Siesta Key Village

A patio with a sun lounger, a table with chairs, and an umbrella.

14. Beach View 100ft To Beach and SPA

Siesta Key Village

A small, single-story building with a porch, surrounded by tropical vegetation.

15. BlueDolphin Cottage Walk To Siesta Beach

Siesta Key Village

A modern living room with a sofa, a coffee table, and a TV. There are windows with blinds, a door, and a kitchen area visible.

16. Pineapple Paradise 1 13 min to Beach Fire Pit

Central Sarasota

฿13,416 total

includes taxes & fees

10 Nov - 11 Nov

A wooden-paneled room with a round table and four chairs, a flat-screen TV mounted on the wall, and a refrigerator in the background.

17. Sun Outdoors Sarasota

Fordville

฿17,068 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with white cabinets, a built-in oven, and a microwave. There is a dining area with a wooden table set for two, blue plates, and wine glasses. A ceiling fan is visible in the living room area.

18. Beach Road

Siesta Key

A kitchen with white cabinets, a granite countertop, and a large bowl. There is a dining area with a table and chairs, and a view of the ocean through a window.

19. Unwind Poolside + Walk to Beach! Sarasota Retreat

South Village

"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "

Eleuterio

฿20,524 total

includes taxes & fees

23 Nov - 24 Nov

A covered porch with a glass table and chairs, a painting on the wall, and a view of the outdoors.

20. 4 Mi to Dtwn! Studio w/ Screened Porch in Sarasota

Ridge Wood Heights

฿8,495 total

includes taxes & fees

22 Nov - 23 Nov

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Find holiday rentals that suit your style

Top Osprey Village Hotel Reviews

A reception area with two reception desks, a blue geometric wall design, and a wooden panel accent.

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Nokomis

10/10 Excellent

Abi

A lobby with a blue sofa, yellow armchairs, a reception desk, and a large white pendant light.

Comfort Suites Sarasota - Siesta Key

Sarasota

10/10 Excellent

Pawel

A hotel with a covered outdoor seating area, palm trees, and a sign reading "HOME 2".

Home2 Suites by Hilton Nokomis Sarasota Casey Key

Nokomis

10/10 Excellent

Artur

A living room with a TV, white cabinets, a sofa, and a balcony with a view.

Escape Coastal Resort on Casey Key

Casey Key

8/10 Good

marie

A hotel lobby with a reception desk, two patterned armchairs, a sofa, a coffee table, and a TV screen.

Best Western Plus Ambassador Suites Venice

Venice

10/10 Excellent

Sharon

A lobby with a reception desk, seating area, and a decorative wall.

Fairfield Inn & Suites by Marriott Venice

Venice

10/10 Excellent

Terence

A spacious lobby with a central seating area, a kitchen in the background, and a large chandelier.

Hampton Inn & Suites Venice Bayside South Sarasota

Gateway

10/10 Excellent

Daniel

A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.

Spark by Hilton Sarasota Siesta Key Gateway

Sarasota

10/10 Excellent

Victoria

Tropical Beach Resorts

South Village

10/10 Excellent

The hotel accommodation was great, clean and comfortable, we had room with balcony which was perfect. We would have our breakfast there, come up from beach and have refreshments, so relaxing. Plenty of staff on hand coffee, tea, lemonade, biscuits, popcorn all available free in reception. Along with videos etc. Lots of quiet areas to sit, pool looked nice, we went to beach, if I could add 1 thing, would be to suggest that guests refrain from playing music on the beach, on one of our days...

tigger

A hotel pool area with lounge chairs and a covered seating area.

Carlisle Inn

Pinecraft

10/10 Excellent

PAUL

A spacious living area with a high ceiling, a sofa set, a coffee table, and a dining area with chairs.

Caretta Landing Sarasota, an Ascend Collection Hotel

Fruitville

10/10 Excellent

Alan

Find out more about Osprey Village

Search for holiday rentals in Osprey Village on Expedia! You can easily find your home rentals, villas, holiday apartments in Osprey Village using one of the methods below:

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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.

Search Holiday Rentals in Osprey Village

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Osprey Village holiday rentals

1. Tropical Beach Resorts

2. Hibiscus Suites - Gateway to Siesta Key

3. A Beach Retreat

4. Captiva Beach Resort

5. Casey Key Resort

6. SeaSpray Resort

7. Siesta Heron Suites & Villas

8. Tiny House Siesta

9. Kon Tiki Inn

10. The Inn On Siesta Key

11. 4 Mi to Siesta Key Beach: Condo w/ Pool Access

12. Beach Tree Cottage,Walk To Beach& Siesta

13. Yellow Palm Cottage, Heart of Siesta Key

14. Beach View 100ft To Beach and SPA

15. BlueDolphin Cottage Walk To Siesta Beach

16. Pineapple Paradise 1 13 min to Beach Fire Pit

17. Sun Outdoors Sarasota

18. Beach Road

19. Unwind Poolside + Walk to Beach! Sarasota Retreat

20. 4 Mi to Dtwn! Studio w/ Screened Porch in Sarasota

Find holiday rentals that suit your style

Top Osprey Village Hotel Reviews

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

10/10 Excellent

Find out more about Osprey Village

Frequently Asked Questions

Can I find a holiday rental in Osprey Village?

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

How many holiday rentals will I find in Osprey Village?

What can I see and do in Osprey Village?

What are holiday rentals like in Osprey Village?