Location

Dates

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Vacation rentals in South Pasadena, Florida, United States

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)

$2,322.12 USD total for 7 nights

Nov 7 – 14, 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

$175 – $927/ night(excl. fees & taxes)

BlueJay's Nest: Game Room, King Bed, Walk to Water image 2

BlueJay's Nest: Game Room, King Bed, Walk to Water image 1

BlueJay's Nest: Game Room, King Bed, Walk to Water image 3

BlueJay's Nest: Game Room, King Bed, Walk to Water image 4

BlueJay's Nest: Game Room, King Bed, Walk to Water image 5

BlueJay's Nest: Game Room, King Bed, Walk to Water

2 bedrooms·1 bath

Clearwater • Florida

5(30 reviews)

$8,079.50 USD $7,446.70 USD total for 28 nights

Nov 7 – Dec 5, 2026

BlueJay's Nest: private retreat w/ yard and patio image 1

BlueJay's Nest: private retreat w/ yard and patio image 2

BlueJay's Nest: private retreat w/ yard and patio image 4

Full bath with light-up mirror and extra supplies.

BlueJay's Nest: private retreat w/ yard and patio

2 bedrooms·1 bath

Clearwater • Florida

5(67 reviews)

$6,437.61 USD $5,933.90 USD total for 28 nights

Nov 7 – Dec 5, 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

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

$3,101.14 USD total for 7 nights

Nov 7 – 14, 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

$2,323.24 USD total for 7 nights

Nov 7 – 14, 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)

$3,269.76 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)

$1,892.44 USD total for 7 nights

Nov 7 – 14, 2026

Your private heated pool

Welcome to A Villa Paradise

Bright coastal charm awaits

Comfortable coastal living

Backyard just steps away

A Villa Paradise

3 bedrooms·2 baths

Holmes Beach • Florida

$2,030.30 USD total for 7 nights

Nov 28 – Dec 5, 2026

Welcome to Bird of Paradise Villa

One of six unique Island Garden Villas

Completely remodeled tropical villa

Bird of Paradise entryway

Comfortable and cozy sofa

Bird of Paradise Villa

2 bedrooms·2 baths

Holmes Beach • Florida

$1,441.95 USD total for 7 nights

Nov 7 – 14, 2026

Open seamless floor plan

Welcome to Blue Agave Villa

Newly remodeled dreamy villa

Blue Agave Villa

2 bedrooms·2 baths

Holmes Beach • Florida

5(1 review)

$1,441.95 USD total for 7 nights

Nov 7 – 14, 2026

Welcome to Hibiscus Villa

Designer furnishings

Dining room for 4

Beautiful mid-century modern

Hibiscus Villa

1 bedroom·1 bath

Holmes Beach • Florida

$1,632.73 USD total for 7 nights

Dec 6 – 13, 2026

Thoughtfully styled living area

Welcome to Plumeria Villa

Charming private patio retreat

Sunlit living room with cozy sectional

Plumeria Villa

1 bedroom·1 bath

Holmes Beach • Florida

$1,984.76 USD total for 7 nights

Nov 20 – 27, 2026

Welcome to Palm Villa

All new furnishings

Newly remodeled dreamy villa

Palm Villa

2 bedrooms·2 baths

Holmes Beach • Florida

$1,614.27 USD total for 7 nights

Nov 14 – 21, 2026

Relax on the patio

Welcome to Orchid Villa

Beautifully designed

Coastal blue hues

Cable TV in the living room

Orchid Villa

2 bedrooms·2 baths

Holmes Beach • Florida

$1,614.27 USD total for 7 nights

Nov 7 – 14, 2026

Pompano Palms

3 bedrooms·3½ baths

Palmetto • Florida

$71/ night(excl. fees & taxes)

Stunning private yard and pool

Huge Holmes Beach home

So close to the beach

Spacious and welcoming foyer

Beachy Blue

4 bedrooms·4 baths

Holmes Beach • Florida

$4,098.13 USD total for 7 nights

Nov 27 – Dec 4, 2026

Resort-style relaxation in your own backyard

Sparkling and inviting year-round

Welcome to Aquamarine Oasis

Airy and light-filled space

Coastal-inspired kitchen with wraparound counters

Aquamarine Oasis

3 bedrooms·2½ baths

Holmes Beach • Florida

$2,255.54 USD total for 7 nights

Nov 9 – 16, 2026

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

6 bedrooms·3½ baths

Tampa • Florida

5(55 reviews)

$5,989.00 USD $5,546.04 USD total for 3 nights

Nov 7 – 10, 2026

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

6 bedrooms·4 baths

Tampa • Florida

$3,627.68 USD total for 3 nights

Nov 7 – 10, 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

Holmes Beach • Florida

5(2 reviews)

$2,954.67 USD total for 7 nights

Nov 27 – Dec 4, 2026

Relax by the fire pit and enjoy sunset views in this private backyard

Let the kids play putt putt golf, bocce ball and more while you relax in the refreshing pool. Summertime paradise awaits!

The Salty Palm

3 bedrooms·2 baths

Bradenton • Florida

5(43 reviews)

$1,052.56 USD total for 3 nights

Nov 7 – 10, 2026

Tampa Bay 1BR Suite with Pool & Beach Access image 1

Tampa Bay 1BR Suite with Pool & Beach Access image 2

Tampa Bay 1BR Suite with Pool & Beach Access image 3

Tampa Bay 1BR Suite with Pool & Beach Access image 4

Tampa Bay 1BR Suite with Pool & Beach Access image 5

Tampa Bay 1BR Suite with Pool & Beach Access

1 bedroom·1 bath

Tampa • Florida

$828.07 USD total for 3 nights

Nov 7 – 10, 2026