Home Vacation Home Rentals By Owner In Pensacola, FL

Showing 40 Of 979 Vacation Rentals
Slider Thumb

$225.52

/ Nightly
Private Vacation Home

The Ginkgo Suite- 1st floor

Pensacola, Florida, United States

One-Bedroom Suite | Main HousebrbrThe Ginkgo Room is a one-bedroom, one-bath suite on the main level of the historic house, overlooking a 100+ year-old ginkgo tree.brbrWarm, inviting, and quietly elegant, guests enjoy a private bedroom and bath with access to shared common spaces on the main floor.brbr**The Ginkgo Room may be rented individually or with the Magnolia Suite. When rented separately, the connecting door is securely locked to ensure privacy.brbrOnce forgotten, an estate has been gently reawakened.brbrWelcome to The Timekeeper Stay & Gardens, a thoughtfully restored historic retreat nestled in the heart of downtown Pensacola, Florida. Surrounded by quiet, blooming gardens, this is a place where time is lovingly kept and beauty unfolds at an unhurried pace.brbrThe estate is comprised of several distinct, private accommodations—each individually listed yet connected by a shared sense of history, craftsmanship, and calm. Original details have been preserved, restoration has been done with care, and every space offers views into the surrounding gardens, where century-old trees stand as quiet witnesses to the passing years.brbrWhether you’re here for a romantic escape, a restorative stay, or a moment to slow down, come stay a while.brbrbr**Spaces may be booked individually or together for a full-property experience.brbrGuests will access the Ginkgo Suite via a private, coded entry for self check-in. Your unique access code will be provided prior to arrival.brbrThe suite includes a private bedroom and en-suite bath, along with access to the shared common areas of the main house and the surrounding gardens.brbrI am off property, but nearby, and readily available if you need anything or have questions during your stay. Guests enjoy self check-in and complete privacy.brHOUSE RULES br1. NO PARTIES. Quiet hours 9pm-8am.br2. NO SMOKING. If you smoke/vape, do so outside away from the house and porches, and discard of any butts in the outside trash. br3. NO PETS.br4. FLOORING. The flooring in this home is original hardwood. Please wipe up any spills right away to avoid damage. br5. FURNITURE. Do not move furniture or slide it across the floors.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb

$201.28

/ Nightly
Private Vacation Home

The Magnolia Suite - 1st floor

Pensacola, Florida, United States

The Magnolia SuitebrOne-Bedroom Suite | Main HousebrbrOverlooking the estate’s heritage magnolia, this one-bedroom, one-bath suite sits on the main level of the historic house. Soft light, garden views, and preserved details create a refined yet comfortable stay. Guests enjoy access to shared main-floor common areas. The suite may be booked alone or with the Ginkgo Room, connected by a lockable pass-through door for flexibility and privacy.brbrOnce forgotten, an estate has been gently reawakened.brbrWelcome to The Timekeeper Stay & Gardens, a thoughtfully restored historic retreat nestled in the heart of downtown Pensacola, Florida. Surrounded by quiet, blooming gardens, this is a place where time is lovingly kept and beauty unfolds at an unhurried pace.brbrThe estate is comprised of several distinct, private accommodations—each individually listed yet connected by a shared sense of history, craftsmanship, and calm. Original details have been preserved, restoration has been done with care, and every space offers views into the surrounding gardens, where century-old trees stand as quiet witnesses to the passing years.brbrWhether you’re here for a romantic escape, a restorative stay, or a moment to slow down, come stay a while.brbrbr**Spaces may be booked individually or together for a full-property experience.brbrGuests will access the Magnolia Suite via a private, coded entry for self check-in. Your unique access code will be provided prior to arrival.brbrbrThe suite includes a private bedroom and en-suite bath, along with access to the shared common areas of the main house and the surrounding gardens.brbrI am off property, but nearby, and readily available if you need anything or have questions during your stay. Guests enjoy self check-in and complete privacy.
Bed 1

Bed

Bath 1

Bath

Slider Thumb

$277.62

/ Nightly
Private Vacation Home

The Garden Cottage at The Timekeeper Stay & Gardens

Pensacola, Florida, United States

The Garden CottagebrPrivate One-Bedroom Cottage | Full KitchenbrbrTucked quietly within the gardens, this cottage is a fully private 1BR/1BA retreat surrounded by greenery and calm. This standalone cottage features a full kitchen, ideal for longer stays or guests seeking independence. With garden views from every angle, it offers peaceful seclusion while remaining part of the greater Timekeeper estate-brperfect for couples, creatives, or anyone seeking quiet comfort in downtown Pensacola.brbrA Once Forgotten Estate Has Been Reawakened.brbrIntroducing The Timekeeper Stay & Gardens, a thoughtfully restored retreat nestled in the heart of Pensacola, Florida. Where beauty blooms in quiet gardens and time has been gently kept. brbrThe estate is comprised of several distinct, private accommodations—each individually listed yet connected by a shared sense of history, craftsmanship, and calm . Original details have been preserved, restoration has been done with care, and every space offers views into the surrounding gardens, where century-old trees stand as quiet witnesses to the passing years.brbrWhether you’re here for a romantic escape, a restorative stay, or a moment to slow down, come stay a while.brbrbr**Spaces may be booked individually or together for a full-property experience.brbrGuests will access the Garden Cottage via a private, coded entry for self check-in. Your unique access code will be provided prior to arrival.brbrI am off property, but nearby, and readily available if you need anything or have questions during your stay. Guests enjoy self check-in and complete privacy.brHOUSE RULESbr1. NO PARTIES. Quiet hours 9pm-8am.br2. NO SMOKING. If you smoke/vape, do so outside away from the house and porches, and discard of any butts in the outside trash.br3. NO PETS.br4. FLOORING. The flooring in this home is original hardwood. Please wipe up any spills right away to avoid damage.br5. FURNITURE. Do not move furniture or slide it across the floors.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb

$273.64

/ Nightly
Private Vacation Home

The Carriage house at The Timekeeper Stay & Gardens

Pensacola, Florida, United States

The Carriage HousebrOne-Bedroom Suite | Second Level | Full KitchenbrbrThis is a charming second-level suite, thoughtfully restored from a historic carriage house.brThis one-bedroom, one-bath space includes a full kitchen, offering comfort and convenience with beautiful views overlooking the grounds below. Light-filled and private, the Carriage House blends historic character with modern ease.brbrA Once Forgotten Estate Has Been Reawakened.brbrIntroducing The Timekeeper Stay & Gardens, a thoughtfully restored retreat nestled in the heart of Pensacola, Florida. Where beauty blooms in quiet gardens and time has been gently kept. brbrThe estate is comprised of several distinct, private accommodations—each individually listed yet connected by a shared sense of history, craftsmanship, and calm . Original details have been preserved, restoration has been done with care, and every space offers views into the surrounding gardens, where century-old trees stand as quiet witnesses to the passing years.brbrWhether you’re here for a romantic escape, a restorative stay, or a moment to slow down, come stay a while.brbrbr**Spaces may be booked individually or together for a full-property experience.brbrGuests will access the Carriage House via a private, coded entry for self check-in. Your unique access code will be provided prior to arrival.brbrI am off property, but nearby, and readily available if you need anything or have questions during your stay. Guests enjoy self check-in and complete privacy.
Bath 1

Bath

Sleep 3

Sleeps

Slider Thumb
Exceptional(8)

$338.58

/ Nightly
Private Vacation Home

Serenity Reef on Perdido Key!

Pensacola, Florida, United States

Summary:brbrTop Amenities: 1 mile from Perdido Key Beachbrbr Close to local restaurants & grocery storesbrbr Free WiFi throughout the homebrbr Parking for 2 cars + garage accessbrbr Sleeps up to 10 guestsbrbr Outdoor grill & patio for relaxing mealsbrbr Close to popular attractions (Flora-Bama, Big Lagoon State Park, OWA Amusement Park)brbrbrbrThe Space:brbrSerenity Reef invites you to unwind and soak up the beauty of the Florida coast. With 4 spacious bedrooms and 3.5 bathrooms, this modern retreat is designed to fit families or groups of up to 10 guests, offering the perfect space for both relaxation and adventure.brbrbrbrInside, the bright and open living area provides a cozy space to unwind with a large flat-screen TV and plenty of seating for everyone. The kitchen comes fully equipped with modern appliances, perfect for preparing meals or quick snacks during your stay.brbrbrbrEach bedroom is designed with comfort in mind, featuring soft linens and plush pillows. The master suite offers a king-size bed, while the other rooms provide cozy queen-size and bunk beds, making it ideal for families with kids.brbrbrbrStep outside to a serene patio with a grill, perfect for dining al fresco and enjoying the fresh Florida air. Whether you're enjoying a meal, a drink, or simply taking in the surroundings, this space is an ideal place to relax.brbrbrbrYou'll find everything you need just a short drive away – from the sandy beaches of Perdido Key to exciting local attractions. Plus, with free WiFi, parking, and convenient access to all the area's highlights, Serenity Reef is the perfect destination for your next getaway.brbrbrbrOther Things to Note:brbr35 minutes to Pensacola International Airportbrbrbrbr30 minutes to downtown Pensacolabrbrbrbr5 minutes away from Johnson's Beachbrbrbrbr10 minutes away from Big Lagoon State Parkbrbrbrbr45 minutes away from Pensacola Beachbrbrbrbr15 minutes away from the National Naval Aviation Museumbrbrbrbr10 minutes away from the famous Flora-Bama Barbrbrbrbr30 minutes away from OWA Amusement ParkbrbrbrbrMinutes away from local restaurants and grocery storesbrbrbrbrbrbrFree WifibrbrClose to Naval Air Station PensacolabrbrNo pets and no smoking allowedbrbrMust be 25 years or older to book.
Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(55)

$237.6

/ Nightly
Private Vacation Home

Beautiful Historic Downtown Pensacola Charmer

Pensacola, Florida, United States

Fully renovated, historic downtown Pensacola home that`s less than 10 minutes to the Beach. All the quaint charm with modern features and finishes. Curated designer materials and furniture. This home is fully equipped for leisure or business travel. Features all new king-size, quality bedding, new bikes. Walk to downtown, the bay center, many dining and nightlife options or head to the beach. The home is equipped with full kitchenware and appliances and includes laundry room. Sit back and enjoy!brbrThis historic Gertrude Simpson Taylor 1908 home has been fully renovated with designer materials, recessed lighting and all the modern comforts. Beautiful, huge dine in kitchen that is fully stocked for you. Washer and dryer included. Enjoy the expansive porches and sunsets. Brand new bikes and a New Orleans style courtyard with lighting and new furniture. 65` Smart TV and HiFi sound.brbrGuests can access the entire housebrbrThis home is perfectly situated in downtown and next to the Bay Center. You can walk or ride very easily. Enjoy the quiet historic neighborhood with lots of charm. Walk to happening Palafox street or take a short ride to the beachbrbrOff street parking comes with the rental and there is lots of additional safe, lit street parking as neededbrbrOff street parking and full laundry. Updated finished and a fully stocked kitchen. Brand new bikes and a New Orleans style courtyard with lighting and new furniture. 65` Smart TV and HiFi sound.brHouse Rules: brNo more than 4 total overnight guests. brNo more than 8 total people in the house at any time.brNo Parties ever.brNo Smoking in the home.brNo loud noise after 10 pm. brNo shooting of fireworks on the property.brThoroughly clean any utensils, pots and pans after use. brPut things back where you got them. brIf you break something or find something broken, contact the host. brThere are two bikes with locks for your use. If they are damaged, lost or stolen for any reason a $300 fee will applybrbrDeparture: brLeave linens on the bed.brPlace all used towels in the bathtub. brSet thermostat to 60° in winter and 80° in summer. brLoad dishwasher and start. brMake sure all pots and pans are clean. brTurn off all lights. brTurn off TV and electronics brTake out all trash and recyclables brbrThe cleaning team arrives promptly at 11:00am on your check out date so please be respectful of their time. Please don`t hesitate to call us for any reason.brbrHOT TUB RULES AND FINES:brbrABSOLUTELY NO SAND OR GLASS IN THE TUB. IF THERE IS SAND OR GLASS IN THE TUB POST STAY, A NON-NEGOTIABLE $200 FEE WILL BE CHARGED TO YOUR CREDIT CARD FOR DRAINING, CLEANING AND REFILLING THE TUB. brYOU MUST RINSE BEFORE ENTERING THE TUBbrNO SUNSCREEN IN TUBbrFILL AND USE THE WASHPAN FOR CLEANING FEET BEFORE ENTERING THE TUBbrMAKE SURE JETS ARE OFF WHEN NOT USINGbrCAREFULLY PLACE THE TOP BEHIND THE TUB WHEN IN USE AND REPLACE IT WHEN FINISHEDbrNO FOOD OR DRINK IN THE TUBbrNEVER DRAIN THE TUBbrIF YOU ARE UNSURE OF ANY OF THE OPERATIONS, UNPLUG THE TUB
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(17)

$175.1

/ Nightly
Private Vacation Home

Minutes from the Beach!
A-Frame at The Point

Pensacola, Florida, United States

Unwind at this modern home just minutes from the beach. This home is located on Innerarity Point, a locals-only spot with restaurants and grocery stores within a short drive. This home was lovingly built with exposed beams for a luxurious yet charming feel. Take an early morning stroll to Innerarity Point Park with beautiful oaks for shade, walking paths, playground equipment and pier. Enjoy the nightlife at FloraBama or The Jellyfish. A short drive to historic downtown Pensacola.brbrRelax with the whole family at this unique yet spacious (over 1150 sq feet) home. The upstairs bedroom has its own private full bathroom. Enjoy your morning coffee in the quiet backyard or fire up the grill for a home made dinner. brbrThe kitchen is fully stocked with all the essentials. Each bedroom has its own smart TV; guest must use their own log-in for their streaming TV services.brbrLooking to go to the Beach There are multiple public beach accesses on Perdido Key and Johnson's Beach on the Gulf Islands National Seashore is less than 10 minutes down the road. Additionally, Innerarity Point Park has beautiful sunset and Intercoastal waterway views.brbrbrThe private circle driveway is large enough for two cars.brGuest Entry instructions: This home utilizes a smart lock that requires a unique code to enter. This code is reset after each guest's stay. This home features a Ring doorbell camera that records video and sound.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Home Most popular vacation rentals in Pensacola