Location

Dates

Guests

Vacation rentals in Sarasota, Florida, United States

[Living area] Smart TV with Netflix & Hulu

Waterfront tiny home sits on a private 1.5 acre inland peninsula! The perfect location for bird watching & kayaking around the lake.

[Living area] Doorway to the left leads into the main bedroom.

[Kitchen] Fully stocked & equipped kitchen with large farm sink and convection cooktop.

[Living area] French doors open up into the spacious backyard. Sofa converts into a bed for additional sleeping space.

@Shellmateisland |tiny home| island| bikes| kayaks

1 bedroom·1 bath

Sarasota • Florida

553,00 $ USD total for 3 nætter

20.–23. okt. 2026

The Casa Blanca resort beach offers free cabanas

Olympic sized heated pool

White sandy beaches

Frolicking birds

Private villa with screened porch 2 villas from beach

Sun & Sand ~ “Happy Place Villa” Steps to Beach

2 bedrooms·1 bath

Siesta Key • Florida

5(13 reviews)

1.525,50 $ USD total for 5 nætter

12.–17. nov. 2026

5 min walk to the best Beach in America! image 1

5 min walk to the best Beach in America! image 2

5 min walk to the best Beach in America! image 3

5 min walk to the best Beach in America! image 4

5 min walk to the best Beach in America! image 5

5 min walk to the best Beach in America!

1 bedroom·2 baths

Siesta Key • Florida

3.120,00 $ USD 2.823,00 $ USD total for 30 nætter

20. okt.–19. nov. 2026

Siesta Dunes Pool

Living room - 65" TV, sleeper sofa

Lanai with sliders - "Palm View"

Living room - 65" TV, sleeper sofa

Living room with 65" TV

Palm View at Siesta Dunes

2 bedrooms·2 baths

Siesta Key • Florida

5(15 reviews)

2.580,08 $ USD total for 7 nætter

23.–30. okt. 2026

Our Private Beach with chairs and umbrellas all included!!

Just a day at our private beach

Sandy's Siesta Key Condo

Sandy's Siesta Key Condo

Sandy's Siesta Key Condo

Sandy's Siesta Key Condo

2 bedrooms·1½ baths

Sarasota County • Florida

1.200,01 $ USD total for 7 nætter

8.–15. nov. 2026

506 Siesta

2 bedrooms·2 baths

Sarasota • Florida

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

3 bedrooms·2 baths

Sarasota • Florida

4.89(18 reviews)

1.406,85 $ USD total for 3 nætter

20.–23. okt. 2026

Private beach access is 350 steps from property gate

Incredible Pool

Gated access and covered parking

Enjoy meals inside or on the balcony

Beach, Bay, Food, Fun - 2BD/2BA

2 bedrooms·2 baths

Siesta Key • Florida

4.67(9 reviews)

1.488,48 $ USD total for 5 nætter

20.–25. okt. 2026

Golf Course Condo

Golf Course Condo

Golf Course Condo

Golf Course Condo

Golf Course Condo

Golf Course Condo

2 bedrooms·2 baths

Sarasota • Florida

3.665,00 $ USD total for 30 nætter

20. okt.–19. nov. 2026

Float the day away!

View from our lanai - straight on out!

The sweet life!

Condo with a View on Longboat Key

0 bedrooms·1 bath

Longboat Key • Florida

4.98(122 reviews)

971,80 $ USD total for 3 nætter

21.–24. okt. 2026

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

0 bedrooms·1 bath

Longboat Key • Florida

5(28 reviews)

971,80 $ USD total for 3 nætter

20.–23. okt. 2026

Beautiful Sarasota villa in a quiet tropical setting with a screened lanai for comfortable outdoor living. Surrounded by palm trees and lush landscaping, this peaceful retreat offers privacy and relaxation just minutes from beaches and attractions.

Sarasota Villa with Pool Access Tennis Near Beach image 2

Sarasota Villa with Pool Access Tennis Near Beach image 3

Sarasota Villa with Pool Access Tennis Near Beach image 4

Sarasota Villa with Pool Access Tennis Near Beach image 5

Sarasota Villa with Pool Access Tennis Near Beach

2 bedrooms·2 baths

Sarasota • Florida

5(5 reviews)

1.543,58 $ USD total for 7 nætter

20.–27. okt. 2026

IMG Academy, Heated Pool, Huge Game Room & Golf! image 1

IMG Academy, Heated Pool, Huge Game Room & Golf! image 2

IMG Academy, Heated Pool, Huge Game Room & Golf! image 3

IMG Academy, Heated Pool, Huge Game Room & Golf! image 4

IMG Academy, Heated Pool, Huge Game Room & Golf! image 5

Sunny Bradenton Oasis, Pool/ Near Beaches & Golf!

4 bedrooms·2 baths

Bradenton • Florida

914,17 $ USD 879,76 $ USD total for 3 nætter

8.–11. nov. 2026

balcony + Gulf view

Living room with Gulf view

Beachfront Escape – Private Balcony, Gulf Views image 5

Panoramic Gulf View with Amazing Sunset.

1 bedroom·1 bath

Longboat Key • Florida

4.87(223 reviews)

1.227,18 $ USD total for 3 nætter

16.–19. nov. 2026

Renovated Beach Paradise. Ground Floor unit 64 image 1

Turtle Crawl Inn 64

1 bedroom·1 bath

Longboat Key • Florida

4.88(73 reviews)

932,25 $ USD total for 3 nætter

26.–29. okt. 2026

Right on the beach.Renovated ground Floor unit 63. image 1

Right on the beach.Renovated ground Floor unit 63. image 5

Turtle Crawl Inn 63

0 bedrooms·1 bath

Longboat Key • Florida

4.74(88 reviews)

815,86 $ USD total for 3 nætter

27.–30. okt. 2026

Casa Milly image 1

Casa Milly image 2

Casa Milly image 3

Casa Milly image 4

Casa Milly image 5

Casa Milly

2 bedrooms·1 bath

Bradenton • Florida

5(36 reviews)

600,00 $ USD total for 3 nætter

20.–23. okt. 2026

Our home is in the left side of the picture.

The front of our home.

Established 2019

Craig House with Heated Pool

3 bedrooms·2 baths

Bradenton • Florida

4.8(107 reviews)

1.150,60 $ USD 1.104,12 $ USD total for 5 nætter

30. okt.–4. nov. 2026

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

2 bedrooms·2 baths

Longboat Key • Florida

25.878,00 $ USD total for 120 nætter

20. okt. 2026–17. feb. 2027

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

9 bedrooms·3 baths

Bradenton • Florida

4.572,09 $ USD total for 3 nætter

20.–23. okt. 2026

Located directly on the beach! Morning coffee on the lanai overlooking Gulf and beach!

New living room furniture with views!

Siesta Key Beachfront Condo

Siesta Key Beachfront Condo

Siesta Key Beachfront Condo

Siesta Key Beachfront Condo

2 bedrooms·2 baths

Siesta Key • Florida

3.113,26 $ USD total for 7 nætter

31. okt.–7. nov. 2026

Relax in the spacious living room while enjoying breathtaking Gulf views through floor-to-ceiling sliding glass doors leading out to the screened/glassed lanai

Spacious living room with comfortable leather seating, a large smart TV, and direct access to the screened/glassed lanai.

Beautifully updated gourmet kitchen featuring granite countertops, stainless steel appliances, and plenty of room to prepare meals.

Designed with extended stays in mind, this spacious kitchen offers abundant cabinetry and generous workspace.

The open dining area comfortably seats six and flows seamlessly into the beautifully updated kitchen.

Gulf Front on Siesta Key - Fishermans Haven 403

2 bedrooms·2 baths

Sarasota • Florida

7.734,34 $ USD total for 27 nætter

30. dec. 2026–26. jan. 2027

7th-Floor Water-View Getaway on Siesta Key

7th-Floor Water-View Getaway on Siesta Key

7th-Floor Water-View Getaway on Siesta Key

7th-Floor Water-View Getaway on Siesta Key

7th-Floor Water-View Getaway on Siesta Key

7th-Floor Water-View Getaway on Siesta Key

1 bedroom·1 bath

Siesta Key • Florida

1.318,00 $ USD total for 7 nætter

26. okt.–2. nov. 2026

Backyard Oasis: Dive into relaxation with a sparkling pool and spa, surrounded by lush greenery!

Exterior: Vibrant sunsets and lush greenery await you in this stunning Bradenton retreat!

Living room with leather sofa, chairs and coffee table

Fully equipped kitchen with stainless steel appliances including French Door refrigerator with water and ice maker in door, glass electric stove, oven, microwave, coffee maker, electric tea kettle, dishes, cooking and baking pans, pots

Wood dining table

Heated Pool, Spa, BBQ, Games, Fire Pit, Sleeps 10

3 bedrooms·2 baths

Bradenton • Florida

5(75 reviews)

757,00 $ USD total for 3 nætter

15.–18. nov. 2026