Location

Dates

Guests

Vacation rentals in Longboat Key, Florida, United States

Spectacular sunsets await

Welcome to Blue Tides

Your retreat awaits

Coastal comfort meets modern style

A living space made for gathering

Blue Tides

3 bedrooms·3 baths

Holmes Beach • Florida

$ 14.927,14 USD totaal voor 30 nachten

18 nov – 18 dec 2026

Stunning nighttime landscape

Soak up the sun in your own backyard oasis

Amazing location in Holmes Beach

Welcome to Peaceful Holmes

Peaceful Holmes

3 bedrooms·3 baths

Holmes Beach • Florida

$ 2.985,44 USD totaal voor 7 nachten

28 nov – 5 dec 2026

Beautiful tropical pool

Welcome to Wish Upon a Starfish!

Plenty of living room seating

Dining area and kitchen

Cozy dining area

Wish Upon a Starfish

3 bedrooms·3 baths

Holmes Beach • Florida

$ 2.390,94 USD totaal voor 7 nachten

1–8 dec 2026

Welcome to A Lazy River Day & Night

Open Kitchen, Dining, Living Area Day Side

Day Side New Kitchen, Dining Area with added Food Pantry and Complimentary Beverage Center

A Lazy River - Both Units

4 bedrooms·3½ baths

Holmes Beach • Florida

$ 3.596,24 USD totaal voor 7 nachten

28 nov – 5 dec 2026

Welcome to Bubbles Up

Sprawling 4 bedroom home

Adorable entry awaits

Grand open living space

Gather together with the family

Bubbles Up

4 bedrooms·3½ baths

Holmes Beach • Florida

$ 3.963,96 USD totaal voor 7 nachten

28 nov – 5 dec 2026

Experience the magic of evenings at Hayes House. The fire table creates a warm, welcoming gathering place where family and friends can unwind after a day at the beach or pool.

Relax in your private heated pool within a screened lanai. Whether you're swimming or lounging poolside, this backyard oasis is perfect for every season.

Gather at the Hayes House outdoor bar, complete with seating, a large TV, Bluetooth speakers, and fun coastal décor. It's the perfect spot to enjoy drinks, watch the game, listen to music, or unwind after a day at the beach.

One of the most loved features at Hayes House, the private heated pool offers the perfect escape for cooling off or simply soaking in the Florida sunshine.

Relax in the spacious living room featuring comfortable seating, a large Smart TV, original hardwood floors, and a decorative fireplace—perfect for movie nights, conversations, or unwinding after a day of adventure.

Group Oasis: Pool, Hot Tub & 6 Queen Beds

6 bedrooms·4 baths

Palmetto • Florida

5(4 reviews)

$ 2.126,00 USD totaal voor 3 nachten

29 nov – 2 dec 2026

The Pink Chicken private pool

Relax around the cocktail table

Welcome to the Pink Chicken

Private entrance with electronic lock

The Pink Chicken

3 bedrooms·2 baths

Holmes Beach • Florida

5(1 review)

$ 2.453,71 USD totaal voor 7 nachten

25 nov – 2 dec 2026

Welcome to AMI Beach Hideaway

Indoor/outdoor living at its finest

Elevated island retreat

Step inside this charming home

Welcoming coastal dining space

AMI Beach Hideaway

2 bedrooms·2 baths

Anna Maria • Florida

$ 3.805,18 USD totaal voor 7 nachten

2–9 jan 2027

Salt Therapy Beach Cottage
500 steps to the beach image 1

Salt Therapy Beach Cottage
500 steps to the beach image 2

Salt Therapy Beach Cottage
500 steps to the beach image 6

Salt Therapy Beach Cottage
500 steps to the beach image 3

Salt Therapy Beach Cottage
500 steps to the beach image 13

Salt Therapy Beach Cottage 500 steps to the beach

2 bedrooms·2 baths

Holmes Beach • Florida

$ 13.625,00 USD totaal voor 30 nachten

18 nov – 18 dec 2026

Bird's eye view

Stunning backyard with lazy river pool

Beautiful backyard

High end kitchen

Seating for 7 at the kitchen island

H2O Bungalow

3 bedrooms·3 baths

Anna Maria • Florida

$ 3.989,81 USD totaal voor 7 nachten

30 nov – 7 dec 2026

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

3 bedrooms·3 baths

Holmes Beach • Florida

5(9 reviews)

$ 15.424,71 USD totaal voor 28 nachten

18 nov – 16 dec 2026

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

9 bedrooms·3 baths

Bradenton • Florida

$ 7.466,97 USD totaal voor 3 nachten

18–21 nov 2026

Pool area designed for relaxing and entertaining

Quiet island street just a short walk to the beach

Ultimate relaxation

Inviting front porch

Ocean Minded

3 bedrooms·3 baths

Anna Maria • Florida

$ 3.719,02 USD totaal voor 7 nachten

29 nov – 6 dec 2026

Cozy coastal living with Smart TV & relaxing vibe

Lido Beach Pool & Pavilion, The 25-meter lap pool is open Friday through Sunday, from 10:00 am to 4:30 pm, weather permitting. Fees apply.

Primary queen suite with private ensuite and plenty of natural light

Sunny dining area for morning coffee or family dinners

Lido Key | Steps to Beach, Walk to St. Armands

2 bedrooms·2 baths

Sarasota • Florida

4.97(39 reviews)

$ 1.328,00 USD totaal voor 3 nachten

18–21 nov 2026

Main living room with ample seating, dining today and bright sunshine gracing the windows.

Move the additional seating over to the couch after sitting down for dinner.

Dinner for 4. Quick and easy access to the full size kitchen for home cooked meals while on vacay.

Queen bed, with additional ceiling fans if you like it really cold and of course your very own private full bathroom. Also, ample closet space to fully stretch out.

Lido Key Beach Escape | 2 Private Suites

2 bedrooms·2 baths

Sarasota • Florida

4.95(21 reviews)

$ 1.239,92 USD totaal voor 3 nachten

30 nov – 3 dec 2026

Pompano Palms

3 bedrooms·3½ baths

Palmetto • Florida

$71/ nacht(excl. kosten & belastingen)

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

2 bedrooms·2 baths

Sarasota • Florida

$ 31.480,00 USD totaal voor 120 nachten

18 nov 2026 – 18 mrt 2027

32” TV with streaming device Comfortable couch.

Kitchen, diningroom, livingroom area

Gulf Coast Paradise Hideaway

Queen bed, night stand with usb plug, and lamp. 32”TV with streaming device sits on top of Armoire with plenty of storage. Bedroom does have closet with hangers.

Gulf Coast Paradise Hideaway

Gulf Coast Paradise Hideaway

1 bedroom·1 bath

Palmetto • Florida

$ 989,85 USD $ 911,32 USD totaal voor 7 nachten

18–25 nov 2026

Swim, splash, or float the day away

Laid-back living along the canal

Welcome to H2O 360

Your coastal getaway begins here

Open living space filled with light

H2O 360

3 bedrooms·2 baths

Anna Maria • Florida

$ 3.285,76 USD totaal voor 7 nachten

1–8 dec 2026

Sunset soaks await

Welcome to Casa Azul

Modern island charm awaits

Bright coastal comfort

Relaxation starts here

Casa Azul

4 bedrooms·4½ baths

Anna Maria • Florida

$ 6.067,49 USD totaal voor 7 nachten

28 nov – 5 dec 2026

Chasing the Sun- Downtown Burns Court image 1

Chasing the Sun- Downtown Burns Court image 2

Chasing the Sun- Downtown Burns Court image 3

Chasing the Sun- Downtown Burns Court image 4

Chasing the Sun- Downtown Burns Court image 5

Chasing the Sun- Downtown Burns Court

2 bedrooms·1 bath

Sarasota • Florida

4.95(62 reviews)

$ 1.158,00 USD totaal voor 7 nachten

15–22 dec 2026

Loungers by the pool

Beautiful backyard with pool, hot tub and loungers

Welcome to My Mistress!

My Mistress

3 bedrooms·3 baths

Anna Maria • Florida

$ 3.828,57 USD totaal voor 7 nachten

7–14 dec 2026

Welcome to Beach Don't Kill My Vibe

Welcoming foyer and window seat

Prime location just off Pine Avenue

Super close to the beach!

Comfortable sectional in the living room

Beach Don't Kill My Vibe

2 bedrooms·1 bath

Anna Maria • Florida

$175 – $619/ nacht(excl. kosten & belastingen)

Beautiful heated pool

Welcome to Sea Mist!

Perfect location steps to the Bay Beach

Bright and welcoming

Thoughtfully designed for gathering

Sea Mist

3 bedrooms·2 baths

Anna Maria • Florida

$ 3.455,62 USD totaal voor 7 nachten

30 nov – 7 dec 2026