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Vacation rentals in Pensacola

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)

$932.25 USD total for 3 nights

Oct 20 – 23, 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 $1,509.48 USD total for 3 nights

Jun 6 – 9, 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)

$1,235.63 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)

$1,329.00 USD total for 3 nights

Oct 27 – 30, 2026

Coral Creek Beach Haven

4 bedrooms·2 baths

Pensacola • Florida

$1,261.70 USD $1,212.36 USD total for 3 nights

Oct 20 – 23, 2026

Downstairs Half Bath

Bayou Bungalow

3 bedrooms·1½ baths

Milton • Florida

$600.00 USD total for 3 nights

Oct 20 – 23, 2026

Surrey Escape

3 bedrooms·2 baths

Pensacola • Florida

4.98(99 reviews)

$548.20 USD total for 3 nights

Oct 30 – Nov 2, 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

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

$1,567.61 USD total for 3 nights

Oct 20 – 23, 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

$1,133.66 USD total for 3 nights

Oct 20 – 23, 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

$929.04 USD total for 3 nights

Oct 20 – 23, 2026

NAS Pensacola Blue Angels 15 min to Beach Family Friendly

NAS Pensacola Blue Angels 15 min to Beach Family Friendly

NAS Pensacola Blue Angels 15 min to Beach Family Friendly

NAS Pensacola Blue Angels 15 min to Beach Family Friendly

NAS Pensacola Blue Angels 15 min to Beach Family Friendly

NAS Pensacola Blue Angels 15 min to Beach Family Friendly

1 bedroom·1 bath

Pensacola • Florida

$714.66 USD total for 3 nights

Oct 20 – 23, 2026

Family friendly 3 bed home minutes from beaches!

Family friendly 3 bed home minutes from beaches!

Family friendly 3 bed home minutes from beaches!

Family friendly 3 bed home minutes from beaches!

Main Bedroom with en suite bath

Family friendly 3 bed home minutes from beaches!

3 bedrooms·2 baths

Gulf Breeze • Florida

5(36 reviews)

$649.00 USD total for 3 nights

Nov 29 – Dec 2, 2026

Fred’s Nest-Perdido Bay Golf Villa-Close to Beach image 1

Unwind in this inviting Pensacola townhome complete with chic nautical decor and a large smart TV - the ideal spot for movie nights or morning coffee before exploring the Gulf Coast.

Fred’s Nest-Perdido Bay Golf Villa-Close to Beach image 3

Spacious backyard with lush greenery and plenty of room to relax that overlooks the golf course.

Fred’s Nest-Perdido Bay Golf Villa-Close to Beach image 5

Fred’s Nest-Perdido Bay Golf Villa-Close to Beach

2 bedrooms·1½ baths

Pensacola • Florida

5(32 reviews)

$470.40 USD $440.16 USD total for 3 nights

Oct 25 – 28, 2026

Waterfront Home w/Kayaks

Waterfront Home w/Kayaks

Waterfront Home w/Kayaks

Waterfront Home w/Kayaks

Waterfront Home w/Kayaks

Waterfront Home w/Kayaks

3 bedrooms·2 baths

Gulf Breeze • Florida

4.97(38 reviews)

$725.26 USD total for 3 nights

Nov 3 – 6, 2026

Sunset Grill located just down the road. There is also a children play area at the restaurant.

Walkway from the back door to the pool.

Pool and workout room with Sauna and Steamroom

Private Beach within the gated community.

Community view when driving over the Theo Barrs bridge. Notice the private beach and boat on the intercoastal waterway.

Your Ultimate Family Getaway: Perdido Key Florida

3 bedrooms·2½ baths

Perdido Key • Florida

5(15 reviews)

$1,426.40 USD total for 4 nights

Oct 20 – 24, 2026

Perdido Key - Beach and Sparkling Pool. Sleeps 6.

Built-in Bunkbeds

Perdido Key - Beach and Sparkling Pool. Sleeps 6.

2 bedrooms·2 baths

Pensacola • Florida

4.95(66 reviews)

$756.28 USD total for 3 nights

Oct 21 – 24, 2026

GRAND CARIBBEAN #310: A SERENE BEACH GETAWAY...

GRAND CARIBBEAN #310: A SERENE BEACH GETAWAY...

GRAND CARIBBEAN #310: A SERENE BEACH GETAWAY...

GRAND CARIBBEAN #310: A SERENE BEACH GETAWAY...

GRAND CARIBBEAN #310: A SERENE BEACH GETAWAY...

GRAND CARIBBEAN #310: A SERENE BEACH GETAWAY...

1 bedroom·1 bath

Perdido Key • Florida

4.91(174 reviews)

$935.00 USD total for 3 nights

Dec 7 – 10, 2026

Fuzzy Pineapple · Monthly Rates Slashed image 1

Fuzzy Pineapple · Monthly Rates Slashed image 2

Fuzzy Pineapple · Monthly Rates Slashed image 3

Fuzzy Pineapple · Monthly Rates Slashed image 4

Fuzzy Pineapple · Monthly Rates Slashed image 5

Fuzzy Pineapple · Monthly Rates Slashed

2 bedrooms·1 bath

Pensacola • Florida

4.94(145 reviews)

$369.00 USD total for 3 nights

Oct 20 – 23, 2026

Fuzzy Crab · Monthly Rates Slashed image 1

Fuzzy Crab · Monthly Rates Slashed image 2

Fuzzy Crab · Monthly Rates Slashed image 3

Fuzzy Crab · Monthly Rates Slashed image 4

Fuzzy Crab · Monthly Rates Slashed image 5

Fuzzy Crab · Monthly Rates Slashed

2 bedrooms·1 bath

Pensacola • Florida

4.99(68 reviews)

$369.00 USD total for 3 nights

Oct 26 – 29, 2026

Wonderful home up on pilings.

Dine Al fresco on our new quiet deck nestled up against a treed area on the side of our home. Enjoy your coffee listening to the birds or a glass of wine in the evening as you relax outdoors.

Private spacious yard.

Enter into the cozy kitchen fully equipped with with everything you need.

Innerarity Hide-A-Way

3 bedrooms·2 baths

Escambia County • Florida

5(13 reviews)

$976.80 USD total for 4 nights

Oct 20 – 24, 2026

Family Villa: Pool, Beach, Bountiful Amenities!

Family Villa: Pool, Beach, Bountiful Amenities!

Family Villa: Pool, Beach, Bountiful Amenities!

Family Villa: Pool, Beach, Bountiful Amenities!

Family Villa: Pool, Beach, Bountiful Amenities!

Family Villa: Pool, Beach, Bountiful Amenities!

4 bedrooms·4 baths

Pensacola • Florida

4.96(51 reviews)

$1,342.15 USD total for 3 nights

Oct 20 – 23, 2026

Gourmet open concept kitchen w upgraded appliances - cook your fave recipes!

Open concept living room w large cozy sofa for relaxing

Full bathroom 1 in primary bedroom suite - spacious double vanity

Community pool & private beach access - Lost Key Golf and Beach Club

Upscale gas fire pit for cozy conversation in cooler evenings

Coastal Oasis @ Lost Key Golf & Beach Club

4 bedrooms·4 baths

Perdido Key • Florida

5(48 reviews)

$1,617.12 USD $1,491.30 USD total for 3 nights

Oct 20 – 23, 2026

View from your porch

Upgraded seating

Less than 10 steps to the pool. Chairs have been upgraded.

Oceanfront | Gated Entry | Pool | King Bed

Oceanfront | Gated Entry | Pool | King Bed

Oceanfront | Gated Entry | Pool | King Bed

2 bedrooms·1 bath

Perdido Key • Florida

$914.00 USD total for 3 nights

Oct 20 – 23, 2026

As the sky turns pink and gold, you slide into water that's still warm from the day — string lights flicker on, and the whole yard feels like it's just for you.

Popcorn's out, Disney's on, and the black leather sofas fit the whole crew — this is where the evening actually happens

Sandwiches piled high, a pitcher of lemonade catching the light — pull up a chair, because this table was built for a crowd that likes to eat together.

Crisp linens, a wide TV, and your beach bag already packed on the bed — this room says the only thing left to do is go

Fully equipped and beach-ready — brew a fresh pot, pack a beach bag, and you're out the door. This bright, modern kitchen makes mornings effortless.

Paradise Breeze

3 bedrooms·2 baths

Gulf Breeze • Florida

$1,076.89 USD total for 3 nights

Oct 20 – 23, 2026