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
$224 – $526/ nacht(excl. kosten & belastingen)
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
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 totaal voor 3 nachten

28 sep – 1 okt 2026

Outdoor dining
Living area
Property grounds
Living area
Living area

Gone Coastal

2 bedrooms·2 baths
Florida

$ 1.090,66 USD totaal voor 3 nachten

5–8 okt 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)

$ 429,27 USD totaal voor 3 nachten

26–29 sep 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)

$ 609,00 USD totaal voor 3 nachten

26–29 sep 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
$70 – $133/ nacht(excl. kosten & belastingen)
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
$65 – $127/ nacht(excl. kosten & belastingen)
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/ nacht(excl. kosten & belastingen)
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
$85 – $186/ nacht(excl. kosten & belastingen)
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
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 totaal voor 3 nachten

26–29 sep 2026

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)

$ 1.040,63 USD totaal voor 3 nachten

26–29 sep 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 totaal voor 3 nachten

26–29 sep 2026

Surrey Escape
Surrey Escape
Surrey Escape
Surrey Escape
Surrey Escape

Surrey Escape

3 bedrooms·2 baths
Pensacola • Florida
4.98(99 reviews)

$ 529,93 USD totaal voor 3 nachten

29 sep – 2 okt 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

$ 660,00 USD totaal voor 3 nachten

26–29 sep 2026

*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 totaal voor 3 nachten

5–8 okt 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 totaal voor 3 nachten

31 okt – 3 nov 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)

$ 1.296,38 USD totaal voor 3 nachten

27–30 okt 2026

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)

$ 453,47 USD totaal voor 3 nachten

27–30 sep 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)

$ 1.629,44 USD totaal voor 4 nachten

27 sep – 1 okt 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 totaal voor 10 nachten

26 sep – 6 okt 2026

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)

$ 914,17 USD totaal voor 3 nachten

26–29 sep 2026

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
$159 – $425/ nacht(excl. kosten & belastingen)