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Vacation rentals in Pensacola

Featured

Waterfront Heron House- the best sunset views

3 bedrooms·3 baths

Pensacola • Florida

4.89(44 reviews)

$708.75 USD total for 3 nights

Nov 15 – 18, 2026

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(92 reviews)

$1,884.38 USD total for 4 nights

Nov 15 – 19, 2026

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)

$462.97 USD total for 3 nights

Nov 16 – 19, 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(225 reviews)

$848.35 USD $798.66 USD total for 3 nights

Nov 15 – 18, 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)

$651.00 USD total for 3 nights

Nov 15 – 18, 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

Nov 15 – 18, 2026

Front sitting area

Front sitting area

Pensacola Retreat | EV Charger | Sleeps 6 image 4

Pensacola Retreat | EV Charger | Sleeps 6 image 5

Pensacola Retreat | EV Charger | Sleeps 6

3 bedrooms·3 baths

Pensacola • Florida

4.92(49 reviews)

$539.00 USD total for 3 nights

Nov 15 – 18, 2026

Front sitting area

Pensacola Retreat | EV Charger | Sleeps 6

Front sitting area

Pensacola Retreat | EV Charger | Sleeps 6

Pensacola Retreat | EV Charger | Sleeps 6

3 bedrooms·3 baths

Pensacola • Florida

$800.10 USD total for 3 nights

Nov 15 – 18, 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)

$1,012.50 USD total for 3 nights

Nov 22 – 25, 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

$1,500.00 USD $1,245.00 USD total for 3 nights

Nov 15 – 18, 2026

pensacola beach sunset

Sunflower Inn * Private Cozy Cottage Near beaches image 2

Sunflower Inn * Private Cozy Cottage Near beaches image 3

Sunflower Inn * Private Cozy Cottage Near beaches image 4

Sunflower Inn * Private Cozy Cottage Near beaches image 5

Sunflower Inn * Private Cozy Cottage Near beaches

1 bedroom·1 bath

Pensacola • Florida

4.89(294 reviews)

$349.00 USD total for 3 nights

Nov 15 – 18, 2026

Casey's Corner

3 bedrooms·2 baths

Pensacola • Florida

4.96(231 reviews)

$444.61 USD total for 3 nights

Nov 15 – 18, 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)

$1,348.15 USD total for 4 nights

Nov 15 – 19, 2026

Property grounds

Gone Coastal

2 bedrooms·2 baths

Florida

$648.28 USD total for 3 nights

Nov 16 – 19, 2026

Relax and soak up the sunsets with a cold beverage in Polywood chaise lounges next to the gorgeous, screened-in, and the heated (year round) pool. Cheers!!

Welcome to The Garden. Our newly built backyard oasis for cooking, conversation, and camaraderie. Fire up the Weber Grill and enjoy the best of coastal life on The Emerald Coast!

Our main living room featuring a 65" 4K HDR Roku TV, Leather furniture, plenty of board games, and space to relax. Bring the streaming creds!

Our heated/cooled game room featuring dual Pop-A-Shot, 30-Game Nintendo Entertainment System, & Foosball Table. Air hockey is the favorite!

Stunning Pensacola Beach and its iconic fishing pier are only minutes away from our property and feature a superb mix of attractions for families, couples, and groups of friends. Spotting sea turtles, rays, sharks, and dolphins is a family favorite!

Emerald Waves Hideaway

3 bedrooms·2 baths

Gulf Breeze • Florida

5(88 reviews)

$1,221.92 USD total for 4 nights

Nov 15 – 19, 2026

Pensacola Bay behind house

Pensacola Bay Dreams

Pensacola Bay Dreams

Pensacola Bay Dreams

4 bedrooms·2½ baths

Gulf Breeze • Florida

$2,121.00 USD total for 3 nights

Nov 15 – 18, 2026

living room off kitchen

main living room

Polynesian Paradise on Canal - heated pool

4 bedrooms·3½ baths

Gulf Breeze • Florida

$2,618.70 USD total for 3 nights

Jan 12 – 15, 2027

back porch/ master bedroom view

Temperature controlled back patio

Waterside Bliss

3 bedrooms·3½ baths

Gulf Breeze • Florida

$1,426.95 USD total for 3 nights

Apr 1 – 4, 2027

Your Dream Getaway Awaits in our Spacious 4-Bedroom Retreat 🏡✨Perfect for families or groups seeking relaxation and togetherness. Your unforgettable stay begins here. 🌟👨‍👩‍👧‍👦 #FourBedroomBliss #GroupGetaway #HomeAwayFromHome

🛋️🍽️ Our living room features a cozy queen pull-out sofa bed for flexible sleeping arrangements, and a dining area with seating for 6, making it perfect for both relaxation and shared meals.

🍽️✨ Share laughter and delicious moments around our accommodating table that seats six. The perfect setting for unforgettable meals and cherished conversations. 🥂🥗 #DineInStyle #MemorableMe

Step into our inviting space where the kitchen seamlessly flows into the dining area. The perfect setting for shared meals, laughter, and unforgettable moments. Welcome to a space designed for togetherness. 🍷🥂 #OpenConceptLiving #DineAndConnect

🍳✨ Step into our fully equipped kitchen, a haven for chefs and foodies alike. Unleash your culinary creativity with top-notch appliances and ample space. Cook, bond, and savor every moment. 🧁👩‍🍳 #KitchenWonders #CookingIn

Clemson House

4 bedrooms·2 baths

Gulf Breeze • Florida

$608.40 USD total for 3 nights

Nov 16 – 19, 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

Nov 15 – 20, 2026

Private backyard pool with loungers and a peaceful, shaded patio retreat

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

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

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

Pet-Friendly Family Getaway Near Two Beaches

3 bedrooms·2 baths

Gulf Breeze • Florida

5(4 reviews)

$931.12 USD total for 3 nights

Jan 18 – 21, 2027

*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

$2,382.45 USD $2,200.17 USD total for 3 nights

Jun 26 – 29, 2027

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)

$1,152.38 USD total for 3 nights

Nov 15 – 18, 2026