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)

1394,40 $ USD total por 7 noches

22–29 oct 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

8340,00 $ USD total por 30 noches

22 oct – 21 nov 2026

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

1318,00 $ USD total por 7 noches

26 oct – 2 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

7734,34 $ USD total por 27 noches

30 dic 2026 – 26 ene 2027

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

3113,26 $ USD total por 7 noches

31 oct – 7 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
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)

1543,58 $ USD total por 7 noches

22–29 oct 2026

Pool
Outdoor dining
Drone view of Crescent Property.
Beachside
Interior

Crescent Siesta Key Unit 406.

2 bedrooms·2 baths
Siesta Key • Florida
5(76 reviews)

4244,25 $ USD total por 7 noches

22–29 oct 2026

Private beach access is 350 steps from property gate
Incredible Pool
Gated access and covered parking
Brand new furnishings make this feel like a retreat
Enjoy meals inside or on the balcony

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

2 bedrooms·2 baths
Siesta Key • Florida
4.67(9 reviews)

1488,48 $ USD total por 5 noches

22–27 oct 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

589,00 $ USD total por 3 noches

22–25 oct 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

462,00 $ USD total por 3 noches

22–25 oct 2026

506 Siesta
506 Siesta
506 Siesta
506 Siesta
506 Siesta

506 Siesta

2 bedrooms·2 baths
Sarasota • Florida
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

1200,01 $ USD total por 7 noches

8–15 nov 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

3900,00 $ USD total por 30 noches

22 oct – 21 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

3120,00 $ USD 2823,00 $ USD total por 30 noches

22 oct – 21 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)

2580,08 $ USD total por 7 noches

23–30 oct 2026

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)

2264,65 $ USD total por 5 noches

22–27 oct 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 total por 3 noches

25–28 oct 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)

1525,50 $ USD total por 5 noches

12–17 nov 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 total por 3 noches

25–28 oct 2026

Screened in patio, table with seating for 8 and 2 bedrooms look out onto pool as well as the main living space.
Well maintained exterior with new roof and hurricane windows.
Master Bedroom, King bed with french doors to pool and screened in patio
Master Bedroom, King bed, ceiling fan and bedside lamps touch control with USB ports.
Master Bath walk in shower

3BR/2B Vacation Pool Home, Nokomis Fl Rental

3 bedrooms·2 baths
Nokomis • Florida
5(3 reviews)

2052,50 $ USD 1872,25 $ USD total por 7 noches

22–29 oct 2026

Exterior
Kings Gate Mobile Home
Kings Gate Mobile Home
Kings Gate Mobile Home
Kings Gate Mobile Home

Kings Gate Mobile Home

1 bedroom·1 bath
Nokomis • Florida

3275,00 $ USD total por 30 noches

22 oct – 21 nov 2026

Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View

1 bedroom·1 bath
Siesta Key • Florida

941,60 $ USD total por 3 noches

22–25 oct 2026

Casa Mar - Unit 25 1 Bedroom 1 Bath
Casa Mar - Unit 25 1 Bedroom 1 Bath
Casa Mar - Unit 25 1 Bedroom 1 Bath
Casa Mar - Unit 25 1 Bedroom 1 Bath
Casa Mar - Unit 25 1 Bedroom 1 Bath

Casa Mar - Unit 25 1 Bedroom 1 Bath

1 bedroom·1 bath
Siesta Key • Florida

1930,40 $ USD total por 7 noches

24–31 oct 2026

Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View

1 bedroom·1 bath
Siesta Key • Florida

941,60 $ USD total por 3 noches

23–26 oct 2026