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Large Historical Home for Groups Walk to Downtown!
Large Historical Home for Groups Walk to Downtown!
Large Historical Home for Groups Walk to Downtown!
Large Historical Home for Groups Walk to Downtown!
Large Historical Home for Groups Walk to Downtown!

Large Historical Home for Groups Walk to Downtown!

6 bedrooms·5 baths
Pensacola • Florida
4.93(90 reviews)

$2,135.75 USD total for 4 nights

Sep 27 – Oct 1, 2026

Inviting Saltwater Pool Oasis
Prime Gulf Breeze House with Saltwater Pool
Spacious Living/Great Room with Large TV
Inviting Screened Porch with Smart TV
Cozy Living Room with Stylish Seating

Prime Gulf Breeze House with Saltwater Pool

4 bedrooms·3 baths
Gulf Breeze • Florida
$425 – $650/ night(excl. fees & taxes)
Pensacola Beach 1 Bed Sleeps 6 Modern Loft
Pensacola Beach 1 Bed Sleeps 6 Modern Loft
Pensacola Beach 1 Bed Sleeps 6 Modern Loft
Pensacola Beach 1 Bed Sleeps 6 Modern Loft
Pensacola Beach 1 Bed Sleeps 6 Modern Loft

Pensacola Beach 1 Bed Sleeps 6 Modern Loft

1 bedroom·1½ baths
Escambia County • Florida
Outdoor dining
Living area
Property grounds
Living area
Living area

Gone Coastal

2 bedrooms·2 baths
Florida
$142 – $1,334/ night(excl. fees & taxes)
*Early Summer Deal* Pensacola Beach Hideaway
*Early Summer Deal* Pensacola Beach Hideaway
*Early Summer Deal* Pensacola Beach Hideaway
*Early Summer Deal* Pensacola Beach Hideaway
*Early Summer Deal* Pensacola Beach Hideaway

*Early Summer Deal* Pensacola Beach Hideaway

3 bedrooms·2 baths
Pensacola Beach • Florida

$1,631.70 USD total for 3 nights

Oct 5 – 8, 2026

Photos showing new landscaping and outdoor furniture.
Sunshine Beach House (heated pool) Pensacola Beach
Sunshine Beach House (heated pool) Pensacola Beach
Latest photo of the back yard with new landscaping and outdoor furniture.
Sunshine Beach House (heated pool) Pensacola Beach

Sunshine Beach House (heated pool) Pensacola Beach

3 bedrooms·2 baths
Pensacola Beach • Florida
4.91(190 reviews)

$1,235.63 USD total for 3 nights

Oct 31 – Nov 3, 2026

BlueSky Beach House (heated pool) Pensacola Beach
BlueSky Beach House (heated pool) Pensacola Beach
Photo of the public beach on the Gulf of Mexico. 5 to 10 minute walk away.
BlueSky Beach House (heated pool) Pensacola Beach
BlueSky Beach House (heated pool) Pensacola Beach

BlueSky Beach House (heated pool) Pensacola Beach

3 bedrooms·2 baths
Pensacola Beach • Florida
4.99(111 reviews)

$1,307.63 USD total for 3 nights

Oct 27 – 30, 2026

Downtown Pensacola Historic Home with a Modern Twist!
Downtown Pensacola Historic Home with a Modern Twist!
Downtown Pensacola Historic Home with a Modern Twist!
Downtown Pensacola Historic Home with a Modern Twist!
Downtown Pensacola Historic Home with a Modern Twist!

Downtown Pensacola Historic Home with a Modern Twist!

2 bedrooms·2 baths
Pensacola • Florida
Open-concept living with Chicago brick floors - walk to Seville Square and Palafox Street
Primary Bedroom
Restored 1918 cottage in downtown Pensacola's Seville Historic District - walk to festivals
Open kitchen flows into living and dining areas - perfect for entertaining in downtown Pensacola
Restored 1918 cottage in downtown Pensacola's Seville Historic District - walk to festivals

Downtown Pensacola Pet Friendly 2BR/6 Guests

2 bedrooms·2½ baths
Pensacola • Florida

$1,924.26 USD total for 3 nights

Sep 23 – 26, 2026

Welcome to Pensa-Cozy!
Large backyard to enjoy time with friends
Cozy livingroom
Outdoor oasis- even the goat wants to come for dinner!
Cool details throughout the house.

Pensa-Cozy

3 bedrooms·1 bath
Pensacola • Florida

$836.64 USD total for 3 nights

Sep 28 – Oct 1, 2026

The Wright Place: Your Perfect Beach Escape
The Wright Place: Your Perfect Beach Escape
The Wright Place: Your Perfect Beach Escape
The Wright Place: Your Perfect Beach Escape
The Wright Place: Your Perfect Beach Escape

The Wright Place: Your Perfect Beach Escape

3 bedrooms·3 baths
Pensacola • Florida
5(220 reviews)

$876.55 USD $824.04 USD total for 3 nights

Sep 28 – Oct 1, 2026

Casa by the Bay
Casa by the Bay
Casa by the Bay
Casa by the Bay
Casa by the Bay

Casa by the Bay

3 bedrooms·2 baths
Gulf Breeze • Florida

$1,700.00 USD total for 10 nights

Sep 23 – Oct 3, 2026

Pensacola sleeps 2 cozy backyard Studio nook in East Hill
Pensacola sleeps 2 cozy backyard Studio nook in East Hill
Pensacola sleeps 2 cozy backyard Studio nook in East Hill
Pensacola sleeps 2 cozy backyard Studio nook in East Hill
Pensacola sleeps 2 cozy backyard Studio nook in East Hill

Pensacola sleeps 2 cozy backyard Studio nook in East Hill

1 bedroom·1 bath
Pensacola • Florida

$712.30 USD total for 3 nights

Sep 23 – 26, 2026

Pensacola • 1BR • Sleeps 2 • Close to Downtown
Pensacola • 1BR • Sleeps 2 • Close to Downtown
Pensacola • 1BR • Sleeps 2 • Close to Downtown
Pensacola • 1BR • Sleeps 2 • Close to Downtown
Pensacola • 1BR • Sleeps 2 • Close to Downtown

Pensacola • 1BR • Sleeps 2 • Close to Downtown

1 bedroom·1 bath
Pensacola • Florida

$576.45 USD total for 3 nights

Sep 23 – 26, 2026

Pensacola 1 Bedroom Sleeps 2 Suite in East Hill
Pensacola 1 Bedroom Sleeps 2 Suite in East Hill
Pensacola 1 Bedroom Sleeps 2 Suite in East Hill
Pensacola 1 Bedroom Sleeps 2 Suite in East Hill
Pensacola 1 Bedroom Sleeps 2 Suite in East Hill

Pensacola 1 Bedroom Sleeps 2 Suite in East Hill

1 bedroom·1 bath
Pensacola • Florida

$643.79 USD total for 3 nights

Dec 31, 2026 – Jan 3, 2027

Vaulted ceilings and coastal hues set the tone for cozy nights in. Sink into the plush sofa, flip on a movie by the fireplace, and let the kids curl up with a beachy throw. A bright, breezy living room made for slowing down together
This is why you came. A fiery Pensacola Beach sunset paints the sky just 15 minutes from your door — the #1 rated beach in the USA. Stroll the pier, feel the warm sand, and let the Gulf Coast work its magic on your whole crew
The spacious master suite offers a king bed dressed in soft coral linens, a cozy reading chair, and a flat-screen TV. A calm, coastal escape with room to spread out — perfect for parents to recharge after a full day of family fun.
A bright, fully-stocked kitchen made for shared meals. Whip up breakfast at the butcher-block bar, sip coffee by the sunny window, or gather the crew for taco night. Stainless appliances and coastal charm make cooking together feel like home.
An open, sun-filled space made for togetherness. Gather the whole crew around the dining table for game nights and family dinners, with the kitchen and living room just steps away. Plenty of seating means no one's left out of the fun

Pet-Friendly Family Getaway Near Two Beaches

3 bedrooms·2 baths
Gulf Breeze • Florida
5(4 reviews)
$170 – $549/ night(excl. fees & taxes)
Tiny Home
Going tiny doesn’t have to mean going without. This gorgeous kitchen features stunning natural white marble countertops and farmhouse sink!
Tiny Home
Tiny Home
Tiny Home

Tiny Home

1 bedroom·1 bath
Pensacola • Florida
5(32 reviews)

$429.27 USD total for 3 nights

Sep 26 – 29, 2026

Vintage Charmer with Tiny Pool Close to Downtown image 1
Vintage Charmer with Tiny Pool Close to Downtown image 2
Vintage Charmer with Tiny Pool Close to Downtown image 3
Vintage Charmer with Tiny Pool Close to Downtown image 4
Vintage Charmer with Tiny Pool Close to Downtown image 5

Vintage Charmer with Tiny Pool Close to Downtown

3 bedrooms·1 bath
Pensacola • Florida
4.88(251 reviews)
$107 – $270/ night(excl. fees & taxes)
Welcome to Dolphina House!
Dolphina House *East Hill * Dog Friendly!
Dolphina House *East Hill * Dog Friendly!
Dolphina House *East Hill * Dog Friendly!
Dolphina House *East Hill * Dog Friendly!

Dolphina House *East Hill * Dog Friendly!

3 bedrooms·1 bath
Pensacola • Florida
4.9(63 reviews)

$692.25 USD total for 3 nights

Sep 23 – 26, 2026

Luxurious new build minutes from beach+downtown
Luxurious new build minutes from beach+downtown
Luxurious new build minutes from beach+downtown
Luxurious new build minutes from beach+downtown
Luxurious new build minutes from beach+downtown

Luxurious new build minutes from beach+downtown

1 bedroom·1 bath
Pensacola • Florida
4.98(292 reviews)

$515.00 USD total for 3 nights

Sep 23 – 26, 2026

THE CRABSHACK: Waterview Retreat in Pensacola
THE CRABSHACK: Waterview Retreat in Pensacola
THE CRABSHACK: Waterview Retreat in Pensacola
THE CRABSHACK: Waterview Retreat in Pensacola
THE CRABSHACK: Waterview Retreat in Pensacola

THE CRABSHACK: Waterview Retreat in Pensacola

2 bedrooms·1 bath
Pensacola • Florida
4.83(117 reviews)

$1,654.44 USD total for 7 nights

Jun 18 – 25, 2027

Open-concept living room with white brick fireplace and bay views at Gulf Breeze waterfront house near Pensacola
Private deck with outdoor furniture and bay views at Bayfront Bliss Gulf Breeze pet-friendly waterfront vacation home
Master Bedroom
Welcoming entry at Bayfront Bliss Gulf Breeze bayfront vacation rental near Pensacola Beach
Private deck with outdoor furniture and bay views at Bayfront Bliss Gulf Breeze pet-friendly waterfront vacation home

Gulf Breeze 3 Bedroom Sleeps 12 Bayfront Retreat

3 bedrooms·3 baths
Gulf Breeze • Florida

$1,732.25 USD total for 3 nights

Sep 23 – 26, 2026

Kitchen with subway tile backsplash and stainless appliances at pet-friendly Gulf Breeze bayfront vacation rental home
Coastal bedroom with comfortable bedding at Bayfront Bliss Gulf Breeze bayfront house near Pensacola Beach Florida
Turquoise Adirondack chairs overlooking the bay at Gulf Breeze bayfront vacation rental
Open-concept living room with bay views at Gulf Breeze waterfront house near Pensacola
Open-concept living room with cozy furniture with sleeper sofa and bay views at Gulf Breeze waterfront house near Pensacola

Gulf Breeze 1 Bedroom Sleeps 4 Bayfront Retreat

1 bedroom·1 bath
Gulf Breeze • Florida

$1,120.73 USD total for 3 nights

Sep 23 – 26, 2026

Comfortable studio unit with murphy bed and kitchenette with Bayfront waterfront views
Waterfront view of bayfront in Guld Breeze with private boatdock
Onlooking studio unit with private patio and brick exterior
Comfortable murphy bed extended with flat screen TV
Comfortable murphy bed extended with flat screen TV with private bathroom showing

Gulf Breeze Bayfront Hideaway! Tiny Home in Gulf Breeze Sleeps 2

1 bedroom·1 bath
Gulf Breeze • Florida

$919.63 USD total for 3 nights

Sep 23 – 26, 2026