Location

Dates

Guests

Vacation rentals in Longboat Key, Florida, United States

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

4 bedrooms·3 baths

Bradenton • Florida

1 693,00 $ USD totalt för 3 nätter

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 totalt för 7 nätter

6–13 dec. 2026

Welcome to Luxe Island Escape

Multi-level decks overlooking the pool

Amazing views from every room

Luxe Island Escape

4 bedrooms·4½ baths

Anna Maria • Florida

5(1 review)

6 396,12 $ USD totalt för 7 nätter

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 totalt för 7 nätter

19–26 dec. 2026

Blissful pool and spa

Huge backyard paradise

Welcome to adorable Anna Margaritas

Welcoming open floor plan

Anna Margaritas

2 bedrooms·2 baths

Anna Maria • Florida

3 114,68 $ USD totalt för 7 nätter

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 totalt för 7 nätter

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 totalt för 7 nätter

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 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 totalt för 3 nätter

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 totalt för 30 nätter

18 nov.–18 dec. 2026

Palmetto House

3 bedrooms·3 baths

Sarasota • Florida

2 593,12 $ USD totalt för 7 nätter

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 totalt för 5 nätter

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 totalt för 7 nätter

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 totalt för 3 nätter

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 totalt för 3 nätter

18–21 nov. 2026

Living room with pullout couch

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 totalt för 3 nätter

29 nov.–2 dec. 2026

Treasure Boat

3 bedrooms·2 baths

Siesta Key • Florida

1 065,75 $ USD totalt för 3 nätter

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 totalt för 28 nätter

15 apr.–13 maj 2027

Commonwealth

4 bedrooms·3½ baths

Siesta Key • Florida

1 496,25 $ USD totalt för 3 nätter

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 totalt för 3 nätter

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 totalt för 5 nätter

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 totalt för 3 nätter

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????

#1 Siesta Key Beach Glass House w/supplies

2 bedrooms·2 baths

Siesta Key • Florida

4.64(58 reviews)

2 141,35 $ USD totalt för 7 nätter

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 totalt för 3 nätter

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 totalt för 7 nätter

7–14 dec. 2026