Huge private pool oasis
Private pool in a tropical setting
Welcome to Saltwater Bliss
Light-filled entry lounge
Perfect settling-in spot

Saltwater Bliss

5 bedrooms·3½ baths
Holmes Beach • Florida

$5,091.42 USD total for 7 nights

Dec 19 – 26, 2026

Private pool in a tropical setting
Huge private pool oasis
Welcome to Saltwater Heaven
Light-filled entry lounge
Perfect settling-in spot

Saltwater Heaven

4 bedrooms·3½ baths
Holmes Beach • Florida

$4,105.51 USD total for 7 nights

Dec 19 – 26, 2026

Sunshine, shade, and ocean breezes
Steps from the sand and sunshine
Bright kitchen with stainless appliances
Easy flow from cooking to gathering
Light-filled room made for relaxing

Beach Daze

2 bedrooms·2 baths
Holmes Beach • Florida
5(1 review)

$2,310.93 USD total for 7 nights

Nov 21 – 28, 2026

Swim, relax, repeat
Short walk to the beach
Updated kitchen with colorful touches
Bold pops of color meet coastal ease

Groovy Guava

2 bedrooms·2 baths
Holmes Beach • Florida
5(1 review)

$1,979.83 USD total for 7 nights

Nov 27 – Dec 4, 2026

Welcome to A Shore Thing
Palm-lined patio built for all-day chilling
Warm, coastal welcome as soon as you step inside
Bright, open cooking space with modern appliances
Dining table for six with natural light

A Shore Thing

3 bedrooms·2 baths
Holmes Beach • Florida

$2,496.79 USD total for 7 nights

Nov 29 – Dec 6, 2026

Freshly harvested coconuts await your arrival for every person in your booking. (No additional charge). So plan to grab a coconut, set up your beach chair and put your feet in the white sands of Anna Maria Island. Cheers to a relaxing getaway!
Cozy but comfortable living room area.
Main bedroom with queen bed with calm blue accents and comfortable bedding.
2nd bedroom with a twin bed over full bunkbed. Closet space for storage.
Back patio sitting area with comfortable plush sectional sofa and arm chairs facing park and small mangrove preserve.

Coconuts included!+Family Friendly!+Close to Beach

2 bedrooms·2 baths
Holmes Beach • Florida
5(1 review)

$2,415.36 USD total for 7 nights

Nov 18 – 25, 2026

Beautiful beachfront pool
Beach lounge chairs available!
Newly updated condo
Open concept design
Spacious kitchen

Cool Breeze

2 bedrooms·2 baths
Holmes Beach • Florida

$2,077.07 USD total for 7 nights

Dec 12 – 19, 2026

Welcome to Key Lime Cottage
Key Lime Cottage half dulpex with private side entrance
Completely remodeled in 2025
Inviting open space

Key Lime Cottage

2 bedrooms·2 baths
Holmes Beach • Florida

$2,451.25 USD total for 7 nights

Jan 2 – 9, 2027

Welcome to Kiwi Cabana
Adorable half duplex in the heart of Holmes Beach
Off-street parking
Inviting and open layout

Kiwi Cabana

2 bedrooms·2 baths
Holmes Beach • Florida

$1,791.51 USD total for 7 nights

Dec 2 – 9, 2026

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the Seaside 21

2 bedrooms·2 baths
Holmes Beach • Florida
4.77(22 reviews)

$2,455.00 USD total for 7 nights

Jan 5 – 12, 2027

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Walk to Beach, Shopping and Restaurants w/ Pool & Elevator

3 bedrooms·2 baths
Holmes Beach • Florida

$2,762.74 USD total for 7 nights

Nov 28 – Dec 5, 2026

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Walking Distance to Beach & Bar w/ Pool

3 bedrooms·2 baths
Holmes Beach • Florida

$2,762.74 USD total for 7 nights

Nov 25 – Dec 2, 2026

Relaxation awaits
Welcome to Grains of Sand
So close to the beach!
Paradise awaits!

Grains of Sand

4 bedrooms·4½ baths
Holmes Beach • Florida

$5,939.48 USD total for 7 nights

Dec 7 – 14, 2026

Private courtyard patio with dining for 4.
Private courtyard patio
Courtyard patio
Exterior detail
Living area

Comforts of Home in Secure Gated Community Just 2 Miles from Anna Maria Island

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

$6,302.00 USD total for 30 nights

Nov 18 – Dec 18, 2026

Welcome to Out of Office!
Plenty of pool side seating
Putting green on side yard
Inviting living room

Out of Office

3 bedrooms·2½ baths
Holmes Beach • Florida
5(1 review)

$2,554.64 USD total for 7 nights

Nov 28 – Dec 5, 2026

La Quinta Sarasota 2 Double | Breakfast, Gym&Pool image 1
La Quinta Sarasota 2 Double | Breakfast, Gym&Pool image 2
La Quinta Sarasota 2 Double | Breakfast, Gym&Pool image 3
La Quinta Sarasota 2 Double | Breakfast, Gym&Pool image 4
La Quinta Sarasota 2 Double | Breakfast, Gym&Pool image 5

La Quinta Sarasota 2 Double | Breakfast, Gym&Pool

1 bedroom·1 bath
Sarasota • Florida

$377.42 USD total for 3 nights

Nov 18 – 21, 2026

La Quinta Sarasota King Std | Breakfast, Gym&Pool image 1
La Quinta Sarasota King Std | Breakfast, Gym&Pool image 2
La Quinta Sarasota King Std | Breakfast, Gym&Pool image 3
La Quinta Sarasota King Std | Breakfast, Gym&Pool image 4
La Quinta Sarasota King Std | Breakfast, Gym&Pool image 5

La Quinta Sarasota King Std | Breakfast, Gym&Pool

1 bedroom·1 bath
Sarasota • Florida

$346.91 USD total for 3 nights

Nov 18 – 21, 2026

Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA

Beachfront Condo on Anna Maria Island, FL, USA

2 bedrooms·2 baths
Anna Maria • Florida

$3,875.00 USD total for 14 nights

Nov 18 – Dec 2, 2026

Our home is in the left side of the picture.
The front of our home.
Sunset View
Established 2019
Entry

Craig House with Heated Pool

3 bedrooms·2 baths
Bradenton • Florida
4.8(107 reviews)

$1,430.60 USD $1,370.12 USD total for 5 nights

Jan 14 – 19, 2027

Soak up the sun!
Dine outside by the pool
Private right side of the duplex
Entryway
Charming coastal decor

Gone Coastal

2 bedrooms·2 baths
Holmes Beach • Florida
5(3 reviews)

$1,812.44 USD total for 7 nights

Nov 18 – 25, 2026

The entire complex is yours!
Gate opens in between the 2 sides
Both sides of the duplex included
First of 2 separate living rooms
All new furniture

Gone Coastal Duplex

4 bedrooms·4 baths
Holmes Beach • Florida

$3,842.11 USD total for 7 nights

Nov 23 – 30, 2026

Welcome to Gone Coastal Too!
Dine outside by the pool
Private left side of the duplex
All new furniture
Charming coastal decor

Gone Coastal, Too

2 bedrooms·2 baths
Holmes Beach • Florida

$2,042.61 USD total for 7 nights

Nov 23 – 30, 2026

Beautiful backyard with pool and tiki bar
Poolside tiki bar
Ground level home
Beautiful ground level beachhouse
Huge dining room table

Gone Coastal 3

3 bedrooms·2½ baths
Holmes Beach • Florida

$2,450.02 USD total for 7 nights

Nov 28 – Dec 5, 2026

Cocktails and Dreams
Welcome to Cocktails and Dreams
Beautiful single story home
Cocktails and Dreams
Gather around for movie night

Cocktails and Dreams

4 bedrooms·4 baths
Holmes Beach • Florida

$7,750.06 USD total for 7 nights

Apr 3 – 10, 2027