Loungers by the pool
Beautiful backyard with pool, hot tub and loungers
Welcome to My Mistress!
Entry way

My Mistress

3 bedrooms·3 baths

$3,012.52 USD total for 7 nights

Nov 7 – 14, 2026

Experience luxury!
Beautiful backyard at any time of the day
Amazing views from the top deck
Almost bay front location

Pier to Pier Paradise

4 bedrooms·4½ baths

$5,359.75 USD total for 7 nights

Nov 16 – 23, 2026

Refreshing dips under open skies
Game room by the pool
Welcome to Pelican Place
Bright and welcoming island retreat

Pelican Place

3 bedrooms·2 baths

$3,554.09 USD total for 7 nights

Dec 5 – 12, 2026

Stunning nighttime landscape
Soak up the sun in your own backyard oasis
Amazing location in Holmes Beach

Peaceful Holmes

3 bedrooms·3 baths

$2,933.74 USD total for 7 nights

Nov 11 – 18, 2026

Welcome to Paradise
Private tropical oasis
Convenient ground level home
Charming beach house

Paradise Pointe

3 bedrooms·2 baths

$3,331.31 USD total for 7 nights

Nov 11 – 18, 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
5(2 reviews)

$5,842.24 USD total for 7 nights

Nov 15 – 22, 2026

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

Out of Office

3 bedrooms·2½ baths
5(1 review)

$2,464.79 USD total for 7 nights

Nov 12 – 19, 2026

Pool area designed for relaxing and entertaining
Quiet island street just a short walk to the beach
Ultimate relaxation

Ocean Minded

3 bedrooms·3 baths

$3,961.50 USD total for 7 nights

Nov 29 – Dec 6, 2026

Enjoy your waterfront pool and spa
Direct beachfront home - No Tan Lines
Elevated beachfront home with pool

No Tan Lines

4 bedrooms·4 baths

$11,011.81 USD total for 7 nights

Dec 11 – 18, 2026

Beautiful elevated home with private yard
Welcome to Rollin' with the Waves
Only five houses to the sand
Your tropical getaway awaits

Rollin' with the Waves

3 bedrooms·2½ baths
5(2 reviews)

$2,954.67 USD total for 7 nights

Nov 27 – Dec 4, 2026

Relaxing saltwater pool area ideal for all-day lounging
Resort-style saltwater pool perfect for cooling off
Inviting retreat with room for friends and family to relax
Welcome to Manatee Manor

Manatee Manor

3 bedrooms·2 baths

$3,360.85 USD total for 7 nights

Nov 14 – 21, 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
5(1 review)

$6,334.58 USD total for 7 nights

Nov 10 – 17, 2026

Sunny Limelight pool
See how close you are to the beach
Welcome to Limelight!
Bright open living space

Limelight

3 bedrooms·2 baths

$3,067.90 USD total for 7 nights

Nov 12 – 19, 2026

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

$1,449.34 USD total for 7 nights

Nov 10 – 17, 2026

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

Key Lime Cottage

2 bedrooms·2 baths

$3,010.05 USD total for 7 nights

Nov 21 – 28, 2026

Stunning modern beach retreat
Oversized heated L-shaped pool
Welcome to Jungalow Beach
Step into paradise
Open-air lanai by the pool

Jungalow Beach

4 bedrooms·6½ baths

$8,680.58 USD total for 7 nights

Nov 13 – 20, 2026

Drift into island relaxation by the water
Blue-water bliss with swaying palms above
Dip your toes while you unwind in style
Welcome to Jungalow Bay

Jungalow Bay

3 bedrooms·3 baths
5(1 review)

$3,768.69 USD total for 7 nights

Nov 11 – 18, 2026

Beautiful huge saltwater pool
Jacaranda Gem
So close to the beach
Newly remodeled coastal home
Dining area with a view!

Jacaranda Gem

3 bedrooms·2½ baths
5(1 review)

$4,095.66 USD total for 4 nights

May 8 – 12, 2027

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
5(2 reviews)

$5,237.89 USD total for 7 nights

Nov 30 – Dec 7, 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

$2,046.30 USD total for 7 nights

Nov 7 – 14, 2026

White Palms gorgeous pool
Welcome to White Palms
Ground level north end home!
Welcoming entryway
Adorable details

White Palms

3 bedrooms·2 baths

$3,269.76 USD total for 7 nights

Nov 8 – 15, 2026

Private heated pool
Whispering Winds by Beach Boutique Rentals
Steps to the Bay!
Stylish living area
Full of character and charm!

Whispering Winds

2 bedrooms·2 baths
5(5 reviews)

$2,895.58 USD total for 7 nights

Nov 7 – 14, 2026

Pool retreat steps from the beach
Float in the sparkling waters
Start every day seaside
Welcome to What a Catch
Sunlit living room with beachy flair

What a Catch

7 bedrooms·7½ baths

$4,128.90 USD total for 4 nights

Nov 9 – 13, 2026

Float the afternoon away
Welcome to Under the Foxtails
Bright, open coastal living space
Stylish space to relax and chat

Under the Foxtails

3 bedrooms·3 baths

$1,960.14 USD total for 7 nights

Nov 7 – 14, 2026