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)

$2,255.45 USD total for 4 nights

Oct 25 – 29, 2026

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)

$508.93 USD total for 3 nights

Oct 20 – 23, 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

Oct 20 – 23, 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)

$621.00 USD total for 3 nights

Oct 20 – 23, 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

$859.04 USD total for 3 nights

Oct 31 – Nov 3, 2026

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

$1,631.31 USD total for 3 nights

Oct 20 – 23, 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
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

$542.20 USD total for 3 nights

Oct 20 – 23, 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

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

$641.42 USD total for 3 nights

Oct 20 – 23, 2026

Welcome to Dolphina House!
Dolphina House *East Hill * 9 Miles to the Beach!
Cozy living room with beachy decor
Dolphina House *East Hill * 9 Miles to the Beach!
Dolphina House *East Hill * 9 Miles to the Beach!

Dolphina House *East Hill * 9 Miles to the Beach!

3 bedrooms·1 bath
Pensacola • Florida
4.87(70 reviews)

$692.25 USD total for 3 nights

Nov 12 – 15, 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)

$480.00 USD total for 3 nights

Oct 25 – 28, 2026

Bedroom #1
You'll enjoy the comfy sectional sofa.
Refinished original hardwood flooring throughout
Plenty of space to stretch out and relax.
You'll enjoy your favorite programs on the 55in smart tv

The Revere House

3 bedrooms·2 baths
West Pensacola • Florida
5(1 review)

$2,544.00 USD total for 30 nights

Oct 27 – Nov 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

Escape to Five Flags Retreat, Pensacola
Main Living Room
Office Area with Wifi Printer, Sofa, Bookcases
Full Kitchen is nicely equipped to enjoy meals at home. All new appliances, dishes, glassware and pots and pans.
Dining table for 8, perfect for your family meals.

Escape to Five Flags Retreat, Pensacola

4 bedrooms·2 baths
Pensacola • Florida
5(47 reviews)

$1,068.75 USD total for 3 nights

Oct 29 – Nov 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)
Casey's Corner
Casey's Corner
Casey's Corner
Casey's Corner
Casey's Corner

Casey's Corner

3 bedrooms·2 baths
Pensacola • Florida
4.96(231 reviews)

$444.61 USD total for 3 nights

Nov 1 – 4, 2026

Large Bay View House w/Huge Deck & 400yr Old Oaks
Large Bay View House w/Huge Deck & 400yr Old Oaks
Large Bay View House w/Huge Deck & 400yr Old Oaks
Large Bay View House w/Huge Deck & 400yr Old Oaks
Large Bay View House w/Huge Deck & 400yr Old Oaks

Large Bay View House w/Huge Deck & 400yr Old Oaks

4 bedrooms·4 baths
Pensacola • Florida
4.88(225 reviews)

$1,218.47 USD total for 4 nights

Nov 8 – 12, 2026

LOVELY 2 BR RETREAT IN THE HEART OF PENSACOLA!!
LOVELY 2 BR RETREAT IN THE HEART OF PENSACOLA!!
LOVELY 2 BR RETREAT IN THE HEART OF PENSACOLA!!
LOVELY 2 BR RETREAT IN THE HEART OF PENSACOLA!!
LOVELY 2 BR RETREAT IN THE HEART OF PENSACOLA!!

LOVELY 2 BR RETREAT IN THE HEART OF PENSACOLA!!

2 bedrooms·2 baths
Pensacola • Florida

$700.00 USD total for 3 nights

Oct 20 – 23, 2026

Outdoor dining
Living area
Property grounds
Living area
Living area

Gone Coastal

2 bedrooms·2 baths
Florida

$731.02 USD total for 3 nights

Oct 20 – 23, 2026

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
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

Oct 20 – 30, 2026

Cozy Pensacola Cottage | 10 Min to Downtown
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Cozy Pensacola Cottage | 10 Min to Downtown
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image

Cozy Pensacola Cottage | 10 Min to Downtown

3 bedrooms·2 baths
Pensacola • Florida

$866.42 USD total for 3 nights

Oct 20 – 23, 2026

Beach to Bay Getaway with Pool image 1
Beach to Bay Getaway with Pool image 2
Beach to Bay Getaway with Pool image 3
Beach to Bay Getaway with Pool image 4
Beach to Bay Getaway with Pool image 5

Beach to Bay Getaway with Pool

4 bedrooms·4 baths
Escambia County • Florida
5(8 reviews)

$5,475.00 USD total for 5 nights

Oct 20 – 25, 2026