Location

Dates

Guests

Vacation rentals in Longboat Key, Florida, United States

Back yard with new pool 15x28 ft

Pool Depth 3ft-5ft

Casa Blanca Ranch Home near Siesta Key Beach

15x28 ft pool with spa/hot tub

New Sun Shelves with pool chaises

Casa Blanca Ranch Home near Siesta Key Beach

3 bedrooms·2 baths

Sarasota • Florida

5(18 reviews)

2.264,65 $ USD ukupno za 5 noći

18. – 23. stu 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 ukupno za 30 noći

18. stu – 18. pro 2026.

Sun Haven House - 4 mi to beach! 2 beds/2 baths image 1

Well equipped kitchen with full size appliances including a dishwasher.

King Size Bed; Nectar mattress, light cotton blanket along with linens

Queen size Nectar mattress in master bedroom with walk-in closet and adjoining bathroom with large shower.

Cozy mood lighting to enjoy tropical nights and conversation with a cool drink or two.

Sun Haven House - 4 mi to beach! 2 beds/2 baths

2 bedrooms·2 baths

Sarasota • Florida

4.040,59 $ USD ukupno za 30 noći

18. stu – 18. pro 2026.

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

2 bedrooms·2 baths

Sarasota • Florida

722,00 $ USD ukupno za 3 noći

18. – 21. stu 2026.

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths

Sarasota • Florida

$150/ noć(bez naknada i poreza)

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 ukupno za 7 noći

29. stu – 06. pro 2026.

506 Siesta

2 bedrooms·2 baths

Sarasota • Florida

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 ukupno za 5 noći

27. stu – 02. pro 2026.

Drone view of Crescent Property.

Crescent Siesta Key Unit 406.

2 bedrooms·2 baths

Siesta Key • Florida

5(76 reviews)

5.422,84 $ USD 5.043,79 $ USD ukupno za 7 noći

20. – 27. pro 2026.

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

2 bedrooms·1 bath

Sarasota • Florida

3.900,00 $ USD ukupno za 30 noći

18. stu – 18. pro 2026.

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

1 bedroom·1 bath

Sarasota • Florida

5(71 reviews)

427,00 $ USD ukupno za 3 noći

28. stu – 01. pro 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 ukupno za 3 noći

22. – 25. stu 2026.

Family home on Golf Course image 1

Family home on Golf Course image 2

Family home on Golf Course image 4

Family home on Golf Course image 5

Family home on Golf Course

4 bedrooms·4 baths

Bradenton • Florida

2.550,00 $ USD ukupno za 5 noći

18. – 23. stu 2026.

Lovely Lakeview Golf Club Condo image 1

Lovely Lakeview Golf Club Condo image 2

Lovely Lakeview Golf Club Condo image 3

Lovely Lakeview Golf Club Condo image 4

Lovely Lakeview Golf Club Condo image 5

Lovely Lakeview Golf Club Condo

2 bedrooms·2 baths

Bradenton • Florida

5(2 reviews)

2.825,00 $ USD ukupno za 30 noći

01. – 31. svi 2027.

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

452,00 $ USD ukupno za 3 noći

18. – 21. stu 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

574,00 $ USD ukupno za 3 noći

18. – 21. stu 2026.

Waterfront Pool Home w/Golf membership, near beach

Waterfront Pool Home w/Golf membership, near beach

Waterfront Pool Home w/Golf membership, near beach

Waterfront Pool Home w/Golf membership, near beach

Waterfront Pool Home w/Golf membership, near beach

Waterfront Pool Home w/Golf membership, near beach

3 bedrooms·2 baths

Bradenton • Florida

8.052,00 $ USD ukupno za 29 noći

18. stu – 17. pro 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 ukupno za 7 noći

01. – 08. pro 2026.

Lake Sarasota image 1

Lake Sarasota image 2

Lake Sarasota image 3

Lake Sarasota image 4

Lake Sarasota image 5

Lake Sarasota

4 bedrooms·2 baths

Sarasota • Florida

4.77(53 reviews)

991,01 $ USD ukupno za 3 noći

06. – 09. pro 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 ukupno za 7 noći

28. stu – 05. pro 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 ukupno za 27 noći

30. pro 2026. – 26. sij 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

1.405,00 $ USD ukupno za 7 noći

11. – 18. pro 2026.

View from front yard

Short walk to fishing pier

Fishing pier before hurricane Milton - now open but shorter than this photo.

Newly remodeled kitchen

Renovated Waterfront Home

Renovated Waterfront Home

3 bedrooms·2 baths

Osprey • Florida

4.4(5 reviews)

1.394,40 $ USD ukupno za 7 noći

18. – 25. stu 2026.

Osprey Harbor Village 216

Osprey Harbor Village 216

Osprey Harbor Village 216

Osprey Harbor Village 216

Osprey Harbor Village 216

Osprey Harbor Village 216

3 bedrooms·2 baths

Osprey • Florida

8.340,00 $ USD ukupno za 30 noći

18. stu – 18. pro 2026.