Location

Dates

Guests

Vacation rentals in North Port, Florida, United States

Secluded sunset views

Large island for dining or entertainment

Centrally located

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 total for 3 nætter

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 total for 3 nætter

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 total for 3 nætter

23.–26. okt. 2026

Sunset from the condo

Walkway to public beach

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 total for 4 nætter

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 total for 30 nætter

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 total for 7 nætter

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

Punta-Paradise!

Punta-Paradise!

Punta-Paradise!

2 bedrooms·2 baths

Punta Gorda • Florida

3.090,00 $ USD total for 30 nætter

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 total for 7 nætter

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 total for 27 nætter

30. dec. 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 total for 7 nætter

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 total for 7 nætter

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 total for 3 nætter

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 total for 3 nætter

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 total for 3 nætter

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 total for 30 nætter

23. okt.–22. nov. 2026

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths

Sarasota • Florida

$150/ nat(exkl. gebyrer & skatter)

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 nætter

25.–28. okt. 2026

Drone view of Crescent Property.

Crescent Siesta Key Unit 406.

2 bedrooms·2 baths

Siesta Key • Florida

5(76 reviews)

4.046,50 $ USD 3.542,24 $ USD total for 7 nætter

23.–30. okt. 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 total for 5 nætter

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 total for 7 nætter

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 total for 5 nætter

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 total for 30 nætter

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 total for 7 nætter

23.–30. okt. 2026