Location

Dates

Guests

Vacation rentals in Osprey, Florida, United States

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 total for 7 nights

Oct 22 – 29, 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 total for 30 nights

Oct 22 – Nov 21, 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

$1,318.00 USD total for 7 nights

Oct 26 – Nov 2, 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 nights

Dec 30, 2026 – Jan 26, 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

$3,113.26 USD total for 7 nights

Oct 31 – Nov 7, 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 nights

Oct 22 – 29, 2026

Drone view of Crescent Property.

Crescent Siesta Key Unit 406.

2 bedrooms·2 baths

Siesta Key • Florida

5(76 reviews)

$4,244.25 USD total for 7 nights

Oct 22 – 29, 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 nights

Oct 22 – 27, 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 for 3 nights

Oct 22 – 25, 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 for 3 nights

Oct 22 – 25, 2026

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

$1,200.01 USD total for 7 nights

Nov 8 – 15, 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 total for 30 nights

Oct 22 – Nov 21, 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 nights

Oct 22 – Nov 21, 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 nights

Oct 23 – 30, 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)

$2,264.65 USD total for 5 nights

Oct 22 – 27, 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 for 3 nights

Oct 25 – 28, 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 nights

Nov 12 – 17, 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 for 3 nights

Oct 25 – 28, 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)

$2,052.50 USD $1,872.25 USD total for 7 nights

Oct 22 – 29, 2026

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

$3,275.00 USD total for 30 nights

Oct 22 – Nov 21, 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 for 3 nights

Oct 22 – 25, 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

$1,930.40 USD total for 7 nights

Oct 24 – 31, 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 for 3 nights

Oct 23 – 26, 2026