Location

Dates

Guests

Vacation rentals in Perdido Key, Florida, United States

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

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 total for 3 nights

Sep 28 – Oct 1, 2026

Property grounds

Gone Coastal

2 bedrooms·2 baths

Florida

$142 – $1,334/ night(excl. fees & taxes)

Going tiny doesn’t have to mean going without. This gorgeous kitchen features stunning natural white marble countertops and farmhouse sink!

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)

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

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 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 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 total for 3 nights

Sep 23 – 26, 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 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

Surrey Escape

3 bedrooms·2 baths

Pensacola • Florida

4.98(99 reviews)

$551.43 USD total for 3 nights

Sep 29 – Oct 2, 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

$675.00 USD total for 3 nights

Sep 23 – 26, 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 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

Casey's Corner

3 bedrooms·2 baths

Pensacola • Florida

4.96(231 reviews)

$462.33 USD total for 3 nights

Sep 27 – 30, 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 total for 4 nights

Sep 27 – 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

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)

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

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