Location

Dates

Guests

Vacation rentals in Milton, Florida, United States

APARTMENT NEAR COAST

APARTMENT NEAR COAST

APARTMENT NEAR COAST

APARTMENT NEAR COAST

APARTMENT NEAR COAST

APARTMENT NEAR COAST

2 bedrooms·1 bath

Milton • Florida

$1,220.00 USD total for 14 nights

Oct 22 – Nov 5, 2026

Downstairs Half Bath

Bayou Bungalow

3 bedrooms·1½ baths

Milton • Florida

$600.00 USD total for 3 nights

Oct 22 – 25, 2026

Nature's Quiet Embrace image 1

Nature's Quiet Embrace image 2

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Nature's Quiet Embrace

2 bedrooms·2 baths

Milton • Florida

4.91(23 reviews)

$594.72 USD total for 3 nights

Oct 28 – 31, 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

Casey's Corner

3 bedrooms·2 baths

Pensacola • Florida

4.96(231 reviews)

$444.61 USD total for 3 nights

Nov 1 – 4, 2026

Cozy Pensacola Cottage | 10 Min to Downtown

Cozy Pensacola Cottage | 10 Min to Downtown

Cozy Pensacola Cottage | 10 Min to Downtown

3 bedrooms·2 baths

Pensacola • Florida

$851.28 USD total for 3 nights

Oct 22 – 25, 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

$690.00 USD total for 3 nights

Oct 22 – 25, 2026

TV moved to where the chair is located and a futon is where the TV is located.

Warm Breeze

4 bedrooms·2 baths

Gulf Breeze • Florida

5(28 reviews)

$729.35 USD total for 3 nights

Oct 28 – 31, 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)

$1,068.75 USD total for 3 nights

Oct 29 – Nov 1, 2026

The Deep Blue Dive-sleeps 16, 10 mins to Beach

The Deep Blue Dive-sleeps 16, 10 mins to Beach

The Deep Blue Dive-sleeps 16, 10 mins to Beach

The Deep Blue Dive-sleeps 16, 10 mins to Beach

The Deep Blue Dive-sleeps 16, 10 mins to Beach

The Deep Blue Dive-sleeps 16, 10 mins to Beach

4 bedrooms·2 baths

Navarre • Florida

5(31 reviews)

$300 – $950/ night(excl. fees & taxes)

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)

$657.00 USD total for 3 nights

Nov 29 – Dec 2, 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

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

$1,214.75 USD total for 3 nights

Oct 22 – 25, 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

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 22 – Nov 1, 2026

Coastal-chic living area with smart TV and fresh, airy decor

Coastal Cottage with Private Beach

Serene bedroom with en-suite access, organized closet & ceiling fan

Fenced backyard with 3-burner gas grill—perfect for BBQ nights

Cozy fenced yard with fire pit, Adirondack lounge & sunset glow

Coastal Cottage with Private Beach

3 bedrooms·2 baths

Gulf Breeze • Florida

$1,223.15 USD total for 4 nights

Nov 23 – 27, 2026

Bright open living room with fireplace, vaulted ceilings, and cozy seating

Charming brick home with spacious lawn, driveway parking, and curb appeal

Private fenced backyard with fire pit and shaded seating area

Bright game room with air hockey, arcade games, and natural light

Bright vaulted kitchen with stainless appliances and ample counter space

Navarre Getaway • Game Room • Near Navarre Beach

4 bedrooms·2 baths

Navarre • Florida

$1,146.75 USD total for 3 nights

Oct 22 – 25, 2026

Bright open living room with fireplace, vaulted ceilings, and cozy seating

Charming brick home with spacious lawn, driveway parking, and curb appeal

Private fenced backyard with fire pit and shaded seating area

Bright game room with air hockey, arcade games, and natural light

Bright vaulted kitchen with stainless appliances and ample counter space

Navarre Getaway • Game Room • Near Navarre Beach

4 bedrooms·2 baths

Navarre • Florida

$1,069.50 USD total for 3 nights

Jan 5 – 8, 2027

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)

$934.51 USD total for 3 nights

Feb 1 – 4, 2027

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

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)

$641.00 USD total for 3 nights

Oct 28 – 31, 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)

$508.93 USD total for 3 nights

Oct 22 – 25, 2026

6min to the Beach, Dogs Fenced Yard, Paddle Board

6min to the Beach, Dogs Fenced Yard, Paddle Board

6min to the Beach, Dogs Fenced Yard, Paddle Board

6min to the Beach, Dogs Fenced Yard, Paddle Board

6min to the Beach, Dogs Fenced Yard, Paddle Board

6min to the Beach, Dogs Fenced Yard, Paddle Board

3 bedrooms·2 baths

Navarre • Florida

4.97(91 reviews)

$1,161.00 USD total for 3 nights

Oct 25 – 28, 2026

Sea Breeze Retreat

3 bedrooms·2 baths

Navarre • Florida

4.4(5 reviews)

$701.12 USD total for 3 nights

Oct 22 – 25, 2026