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Vacation rentals in Sarasota, Florida, United States

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

2 bedrooms·2 baths

Longboat Key • Florida

8.425,50 $ USD gesamt für 60 Nächte

9. Nov. 2026 – 8. Jan. 2027

cozy private patio for your enjoyment

Welcome to Sea Turtle Cove!

Adjustable king size bed. Very comfortable.

Upgraded kitchen space with convection cooktop and lovely light. I added air fryer/toaster oven.

Sea Turtle Cove private oasis near beaches image 5

Sea Turtle Cove private oasis near beaches

1 bedroom·1 bath

Sarasota • Florida

4.94(70 reviews)

432,00 $ USD gesamt für 3 Nächte

9.–12. Nov. 2026

The tiny home sits on a private 1.5 acre inland peninsula!

[Patio] Shared outdoor living space with fire pit

[Living area] This luxury 270sqft craftsman style tiny home is in the ideal location for your beach getaway.

Outdoor dining options available in the screened in lounge.

[Kitchen] Fully equipped kitchen featuring stainless steel appliances & gas cooktop. Coffee maker for all the coffee lovers out there!

·@Tiffanythetinyhome| island | netflix|bike|hammock

1 bedroom·1 bath

Sarasota • Florida

437,00 $ USD gesamt für 3 Nächte

9.–12. Nov. 2026

[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

557,00 $ USD gesamt für 3 Nächte

9.–12. Nov. 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 1.426,63 $ USD gesamt für 5 Nächte

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 gesamt für 30 Nächte

9. Nov. – 9. Dez. 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 gesamt für 7 Nächte

28. Nov. – 5. Dez. 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 gesamt für 7 Nächte

9.–16. 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 gesamt für 3 Nächte

9.–12. Nov. 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 gesamt für 5 Nächte

27. Nov. – 2. Dez. 2026

Drone view of Crescent Property.

Crescent Siesta Key Unit 406.

2 bedrooms·2 baths

Siesta Key • Florida

5(76 reviews)

4.639,75 $ USD 4.442,00 $ USD gesamt für 7 Nächte

9.–16. Nov. 2026

Best Deals on Siesta Key image 1

Best Deals on Siesta Key image 2

Best Deals on Siesta Key image 3

Best Deals on Siesta Key image 4

Best Deals on Siesta Key image 5

Best Deals on Siesta Key

1 bedroom·1 bath

Sarasota • Florida

4.72(155 reviews)

532,00 $ USD gesamt für 3 Nächte

9.–12. Nov. 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 gesamt für 30 Nächte

9. Nov. – 9. Dez. 2026

Lake Sarasota image 1

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Lake Sarasota image 5

Lake Sarasota

4 bedrooms·2 baths

Sarasota • Florida

4.77(53 reviews)

991,01 $ USD gesamt für 3 Nächte

6.–9. Dez. 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 gesamt für 3 Nächte

20.–23. Nov. 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 gesamt für 3 Nächte

9.–12. Nov. 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

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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 gesamt für 7 Nächte

9.–16. Nov. 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

945,81 $ USD 909,82 $ USD gesamt für 3 Nächte

9.–12. 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 gesamt für 3 Nächte

29. Nov. – 2. Dez. 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 gesamt für 3 Nächte

9.–12. Nov. 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 gesamt für 3 Nächte

9.–12. Nov. 2026

Casa Milly image 1

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Casa Milly image 5

Casa Milly

2 bedrooms·1 bath

Bradenton • Florida

5(36 reviews)

600,00 $ USD gesamt für 3 Nächte

9.–12. Nov. 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)

1.437,32 $ USD 1.376,50 $ USD gesamt für 5 Nächte

14.–19. Jan. 2027