Location

Dates

Guests

Vacation rentals in Milton, Florida, United States

Featured

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(90 reviews)

$2,307.32 USD total for 4 nights

Sep 7 – 11, 2026

Featured

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

Sep 7 – 21, 2026

Downstairs Half Bath

Bayou Bungalow

3 bedrooms·1½ baths

Milton • Florida

$600.00 USD total for 3 nights

Sep 7 – 10, 2026

Nature's Quiet Embrace image 1

Nature's Quiet Embrace image 2

Nature's Quiet Embrace image 3

Nature's Quiet Embrace image 4

Nature's Quiet Embrace image 5

Nature's Quiet Embrace

2 bedrooms·2 baths

Milton • Florida

4.91(23 reviews)

$540.96 USD total for 3 nights

Sep 8 – 11, 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)

$1,533.68 USD total for 4 nights

Sep 7 – 11, 2026

Casey's Corner

3 bedrooms·2 baths

Pensacola • Florida

4.96(231 reviews)

$529.88 USD total for 3 nights

Sep 12 – 15, 2026

Free cancellation

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

$645.00 USD total for 3 nights

Sep 7 – 10, 2026

4BR Coastal Retreat - Near Navarre Beach -Sleeps 8 image 1

Vaulted ceilings, endless sectional, kitchen just steps away. This room proves you don't have to choose between space and staying close

Big room, big ceilings, big relaxation. This master delivers

4BR Coastal Retreat - Near Navarre Beach -Sleeps 8 image 4

4BR Coastal Retreat - Near Navarre Beach -Sleeps 8 image 5

4BR Coastal Retreat - Near Navarre Beach -Sleeps 8

4 bedrooms·3 baths

Navarre • Florida

5(3 reviews)

$166 – $595/ night(excl. fees & taxes)

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)

$690.15 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation

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

Sep 7 – 10, 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)

$695.00 USD total for 3 nights

Oct 18 – 21, 2026

Free cancellation

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

Sep 7 – 10, 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

$1,647.58 USD total for 3 nights

Sep 7 – 10, 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

$1,063.10 USD total for 3 nights

Sep 7 – 10, 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

$878.47 USD total for 3 nights

Sep 7 – 10, 2026

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 7 – 10, 2026

Calypso House- East Hill -9 Miles from the Beach!

Another Living Room View

Calypso House- East Hill -9 Miles from the Beach!

Calypso House- East Hill -9 Miles from the Beach!

2 bedrooms·1 bath

Pensacola • Florida

4.98(111 reviews)

$139/ night(excl. fees & taxes)

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 7 – 17, 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

$597.50 USD total for 3 nights

Sep 7 – 10, 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

Sep 7 – 10, 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

$949.20 USD total for 3 nights

Sep 19 – 22, 2026

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

$647.33 USD total for 3 nights

Sep 7 – 10, 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

$537.47 USD total for 3 nights

Sep 7 – 10, 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

$65 – $127/ night(excl. fees & taxes)