Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway

Hubbel Hideaway

4 bedrooms·3 baths
Bradenton • Florida

$ 1.693,00 USD totaal voor 3 nachten

22–25 nov 2026

Huge pool with attached spa
Welcome to Paradise Blu!
Huge tropical yard and pool
Grand living room with views

Paradise Blu

4 bedrooms·4½ baths
Anna Maria • Florida
5(2 reviews)

$ 6.372,74 USD totaal voor 7 nachten

6–13 dec 2026

Welcome to Luxe Island Escape
Multi-level decks overlooking the pool
Main foyer
Amazing views from every room

Luxe Island Escape

4 bedrooms·4½ baths
Anna Maria • Florida
5(1 review)

$ 6.396,12 USD totaal voor 7 nachten

27 nov – 4 dec 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 1
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 2
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 3
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 4
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 5

Villa Blanca | Luxury 5BR Pool Home on Siesta Key

5 bedrooms·4 baths
Sarasota • Florida
5(4 reviews)

$ 10.481,85 USD $ 9.993,42 USD totaal voor 7 nachten

19–26 dec 2026

Blissful pool and spa
Huge backyard paradise
Welcome to adorable Anna Margaritas
Come on in!
Welcoming open floor plan

Anna Margaritas

2 bedrooms·2 baths
Anna Maria • Florida

$ 3.114,68 USD totaal voor 7 nachten

8–15 dec 2026

Resort-style backyard retreat
Welcome to the Veranda on Jacaranda
Tropical vacation begins here
Welcome to beach paradise

The Veranda on Jacaranda

4 bedrooms·3½ baths
Anna Maria • Florida

$ 4.315,99 USD totaal voor 7 nachten

4–11 dec 2026

Where the view becomes your backdrop
Your waterfront pool retreat awaits
Welcome to The Lookout
Your beach escape begins inside

The Lookout

3 bedrooms·2 baths
Anna Maria • Florida
5(2 reviews)

$ 4.995,41 USD totaal voor 7 nachten

30 nov – 7 dec 2026

Perfect place to relax, read a book, and cool down with a dip in crystal clear pool with water fall feature
Front of house
Front entry way
Sun Soaked Paradise - Heated Pool image 5
Living room with ample seating large television.

Sun Soaked Paradise - Heated Pool

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

$ 980,00 USD totaal voor 3 nachten

19–22 nov 2026

Golf Course Condo
Golf Course Condo
Golf Course Condo
Golf Course Condo
Golf Course Condo

Golf Course Condo

2 bedrooms·2 baths
Sarasota • Florida

$ 3.665,00 USD totaal voor 30 nachten

18 nov – 18 dec 2026

Palmetto House
Palmetto House
Palmetto House
Palmetto House
Palmetto House

Palmetto House

3 bedrooms·3 baths
Sarasota • Florida

$ 2.593,12 USD totaal voor 7 nachten

29 nov – 6 dec 2026

Riverfront 4BR: Boat Dock, Heated Pool
Riverfront 4BR: Boat Dock, Heated Pool
Riverfront 4BR: Boat Dock, Heated Pool
Riverfront 4BR: Boat Dock, Heated Pool
Riverfront 4BR: Boat Dock, Heated Pool

Riverfront 4BR: Boat Dock, Heated Pool

4 bedrooms·4 baths
Ellenton • Florida
5(3 reviews)

$ 3.582,01 USD $ 3.264,24 USD totaal voor 5 nachten

11–16 dec 2026

FlipFlopsOn III Vacation Rental • 3 Blocks to the water • FL’s Gulf Coast • Sleeps 6
Your boutique Mediterranean-style 2BR bungalow (4 beds) — resort level comfort + coastal charm!
Your own private resort — located on a serene palm-lined lain in Sarasota’s coveted coastal district!
Half a mile to the Siesta Key, home of Siesta Key Beach — experience the sugar white sands of America’s #1 beach!
A Mediterranean-meets-California retreat where natural textures and curated details invite beautiful living

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Gulf

2 bedrooms·1 bath
Sarasota • Florida
5(2 reviews)

$ 2.178,64 USD totaal voor 7 nachten

28 nov – 5 dec 2026

Sarasota vacation rental
Sarasota vacation rental
Sarasota vacation rental
Sarasota vacation rental
Sarasota vacation rental

Sarasota vacation rental

3 bedrooms·2 baths
Sarasota • Florida

$ 500,00 USD totaal voor 3 nachten

18–21 nov 2026

Landscape lighting and firepit in the front of the house
View of the canal in the back of the house
Sunrise over the pool and covered outdoor seating.
Large pull out sectional facing the fireplace and flatscreen TV
Living room with pull out couch, flatscreen and dining table

Tropi-Casa

4 bedrooms·2 baths
Bradenton • Florida

$ 862,50 USD totaal voor 3 nachten

18–21 nov 2026

Living room with pullout couch
Heated pool
Siesta Key beach
Dusk view of front of building
Front door and porch area

Siesta Key Village Vacation Rental – Walk to Beach

2 bedrooms·1 bath
Sarasota • Florida

$ 745,76 USD totaal voor 3 nachten

29 nov – 2 dec 2026

Treasure Boat
Treasure Boat
Treasure Boat
Treasure Boat
Brand new saltwater pool with full sun to lounge. Heated when requested, always during winter months.

Treasure Boat

3 bedrooms·2 baths
Siesta Key • Florida

$ 1.065,75 USD totaal voor 3 nachten

28 nov – 1 dec 2026

Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

3 bedrooms·2 baths
Siesta Key • Florida
5(26 reviews)

$ 14.950,00 USD totaal voor 28 nachten

15 apr – 13 mei 2027

Commonwealth
Commonwealth
Commonwealth
Commonwealth
Commonwealth

Commonwealth

4 bedrooms·3½ baths
Siesta Key • Florida

$ 1.496,25 USD totaal voor 3 nachten

30 nov – 3 dec 2026

Welcome to your private paradise just minutes from the beach—where relaxation begins the moment you pull in.
Big group? No problem. Our extendable dining table fits up to 10—perfect for family feasts, card nights, or celebratory toasts.
Get the best of both worlds: soft and firm pillows, a private ensuite, blackout blinds for restful sleep, and a king bed made for unwinding. Plus, a smart TV for ultimate relaxation.
When the beach is a few blocks away but the pool is right here. Welcome to the best of both worlds.
Skip the restaurants (if you want to). This kitchen’s got everything: oven, microwave, fridge, dishwasher—even a TV so you don’t miss a moment.

Siesta Key Home | Heated Pool, Theater & Arcade

4 bedrooms·3 baths
Siesta Key • Florida
5(36 reviews)

$ 3.701,06 USD totaal voor 3 nachten

18–21 nov 2026

Heated Saltwater Pool
The pool and surrounding area features enough lighting to enjoy the Florida evenings in style!
Catch the game on the 75" TV from the HOT TUB!
Newly remodeled kitchen with new stainless steel appliances (refrigerator, induction cook top, built in microwave/oven and dishwasher).
Living Room featuring a large sectional sofa and a 55" smart TV. Sit and enjoy the abundance of natural light.

The Funky Fish House

2 bedrooms·2 baths
Sarasota • Florida
4.99(156 reviews)

$ 1.375,73 USD totaal voor 5 nachten

27 nov – 2 dec 2026

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 1
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 2
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 3
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 4
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 5

Lovely room 5 miles from Siesta Key w/ Pool & Spa!

1 bedroom·1 bath
Sarasota • Florida
4.87(60 reviews)

$ 225,00 USD totaal voor 3 nachten

1–4 dec 2026

you never have to cover the windows, it's a private yard.
Pool view from the dining area
TOP WORLD BEACH AND #1 US BEACH
my favorite yellow lifeguard shack. LET'S GO VISIT>>>>> Are you coming????
Dining Room

#1 Siesta Key Beach Glass House w/supplies

2 bedrooms·2 baths
Siesta Key • Florida
4.64(58 reviews)

$ 2.141,35 USD totaal voor 7 nachten

21–28 nov 2026

Cozy Room 5 miles from beaches! image 1
Cozy Room 5 miles from beaches! image 2
Cozy Room 5 miles from beaches! image 3
Cozy Room 5 miles from beaches! image 4
Cozy Room 5 miles from beaches! image 5

Cozy Room 5 miles from beaches!

1 bedroom·1 bath
Sarasota • Florida
4.95(75 reviews)

$ 225,00 USD totaal voor 3 nachten

18–21 nov 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 3
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 2
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 1
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 4
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 5

Blanca Cottage| Private 2BR Pool Home Near Siesta

2 bedrooms·2 baths
Siesta Key • Florida
5(4 reviews)

$ 5.391,20 USD totaal voor 7 nachten

7–14 dec 2026