Secluded sunset views
Large island for dining or entertainment
Centrally located
Guest Registry
Fully equipped kitchen

Herda Hideaway on Little Gasparilla Island

2 bedrooms·2 baths
Little Gasparilla Island • Florida
5(40 reviews)

931,00 $ USD 817,60 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026

Bright, cozy living room with stylish decor and plenty of natural light
Bright modern living room with cozy seating and open kitchen pass-through
Cozy modern living room with stylish decor and open kitchen connection
Bright, stylish living room with TV and open flow to the kitchen
Bright, stylish living room with large windows and cozy seating

Skelatal Listing: Rebecca Drost - 3705 Toulouse Ct, Punta Gorda, Florida 33950

4 bedrooms·3 baths
Punta Gorda • Florida

30.897,00 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026

Canalfront Punta Gorda Retreat w/ Private Pool
Canalfront Punta Gorda Retreat w/ Private Pool
Canalfront Punta Gorda Retreat w/ Private Pool
Canalfront Punta Gorda Retreat w/ Private Pool
Canalfront Punta Gorda Retreat w/ Private Pool

Canalfront Punta Gorda Retreat w/ Private Pool

4 bedrooms·3 baths
Punta Gorda • Florida

26.108,19 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026

Sunset from the condo
Walkway to public beach
Brand new kitchen w/ spices, plenty of plates, pots, pans and utensils.
Start your morning w/ a homemade latte or espresso, French press or just coffee!
Large dining table for dinner or a family game night.

Waterfront Island Condo on Boca Grande-Pure Bliss

2 bedrooms·2 baths
Boca Grande • Florida

1.968,00 $ USD 1.878,60 $ USD gesamt für 4 Nächte

23.–27. Okt. 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 gesamt für 30 Nächte

23. Okt. – 22. Nov. 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 gesamt für 7 Nächte

23.–30. Okt. 2026

One of five satellite pools throughout the community. Our condo is equidistantly located between three of the five satellite pools & the resort style pool.
Tiki bar! The grilled Bang Bang shrimp is our favorite
Resort pool
Punta-Paradise!
Punta-Paradise!

Punta-Paradise!

2 bedrooms·2 baths
Punta Gorda • Florida

3.090,00 $ USD gesamt für 30 Nächte

23. Okt. – 22. 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

1.318,00 $ USD gesamt für 7 Nächte

26. Okt. – 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

7.734,34 $ USD gesamt für 27 Nächte

30. Dez. 2026 – 26. Jan. 2027

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 gesamt für 7 Nächte

23.–30. 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 gesamt für 7 Nächte

31. Okt. – 7. 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

589,00 $ USD gesamt für 3 Nächte

23.–26. Okt. 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 gesamt für 3 Nächte

23.–26. Okt. 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 gesamt für 3 Nächte

25.–28. Okt. 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 gesamt für 30 Nächte

23. Okt. – 22. Nov. 2026

Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths
Sarasota • Florida
$150/ Nacht(zzgl. Gebühren & Steuern)
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 gesamt für 3 Nächte

25.–28. Okt. 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)

4.046,50 $ USD 3.542,24 $ USD gesamt für 7 Nächte

23.–30. Okt. 2026

506 Siesta
506 Siesta
506 Siesta
506 Siesta
506 Siesta

506 Siesta

2 bedrooms·2 baths
Sarasota • Florida
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)

1.488,48 $ USD gesamt für 5 Nächte

23.–28. 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 gesamt für 7 Nächte

8.–15. Nov. 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 gesamt für 5 Nächte

23.–28. Okt. 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

23. Okt. – 22. 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 gesamt für 7 Nächte

23.–30. Okt. 2026