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 total for 5 nights

Nov 18 – 23, 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

Nov 18 – Dec 18, 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 total for 30 nights

Nov 18 – Dec 18, 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

Nov 18 – 21, 2026

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths

Sarasota • Florida

$150/ night(excl. fees & taxes)

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 29 – Dec 6, 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 nights

Nov 27 – Dec 2, 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 total for 7 nights

Dec 20 – 27, 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

Nov 18 – Dec 18, 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

Nov 28 – Dec 1, 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 total for 3 nights

Nov 22 – 25, 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 total for 5 nights

Nov 18 – 23, 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 total for 30 nights

May 1 – 31, 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 total for 3 nights

Nov 18 – 21, 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 total for 3 nights

Nov 18 – 21, 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 total for 29 nights

Nov 18 – Dec 17, 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

Dec 1 – 8, 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 total for 3 nights

Dec 6 – 9, 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 nights

Nov 28 – Dec 5, 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

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 total for 7 nights

Dec 11 – 18, 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 nights

Nov 18 – 25, 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

Nov 18 – Dec 18, 2026