Vacation Condo Rentals By Owner In Key West, FL

$460.85

Two Bedroom Residence

Key West, Florida, United States

Summary:brbrSet on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West.brbrbrbrOn property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise.brbrbrbrDon’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.brbrbrbrThe Space:brbrExperience comfort and convenience in this expansive 2-bedroom condo, featuring a full kitchen, washer/dryer, and your own private balcony retreat. Steps to our onsite marina - at an added cost reserve a private boat slip, or explore ocean activities with our onsite watersports company - Brightwild Adventures.brbrbrbrSleeping arrangements include:brbrBedroom 1: King bed and en-suite bathroom with a double vanity and whirlpool tubbrbrBedroom 2: King bed with en-suite bathroom (separated via lock out door)brbrLiving Area: Queen sleeper sofabrbrbrbrThe fully-equipped kitchen features stainless-steel appliances and includes all cooking essentials. With its open-concept floor plan, the indoor living area seamlessly connects to the private balcony, creating the perfect space for quality time.brbrbrbrGuest Access:brbrPersonalized check in experience!brbrOur luxury resort offers a heated pool, hot tub, on-site marina, restaurant and waterview fitness center.brbrGuests have access to a local Guest Experience Manager (GEM) for recommendations such as on-site bike rentals, water excursions, and our favorite places to eat.brbrbrbrThe Neighborhood:brbrConveniently located on north Key West, Beachside Resort sits on an ideal seven acres of land situated just 10 minutes from Duval Street, ensuring you can be as close or as far from the ‘happenings’ as you’d like. Our hotel contains over 200 guest rooms and suites, two on-property restaurants, a 46,000 gallon pool and Key West’s largest ballroom.brbrbrbrGetting Around:brbrParking Information:brbrGarage parking available on property for $25/night; with electric charging stations.brbrbrbrOn-site Shuttle & Rentals:brbrWe provide a daily shuttle from 9am to 11pm for easy access to Key West and its famed Duval Street attractions or check out our on-site bike & watercraft rentals at Brightwild Adventures.brbrbrbrOther Things to Note:brbr- Host your wedding, corporate, or social events in one of Key West's largest ballrooms with full in-house catering services available.brbr- This property is not pet-friendly.brbr- Private stackable washer/dryer.brbr- Parking is $25 per night, per vehicle plus tax.brbr- All housekeeping services are by request, additional fees may apply. No daily service provided.brbr- Primary Guest must be at least 21 years of age or older in order to reserve this property.

2

Bed

2

Bath

6

Sleeps

$439.88

/ Nightly

Condo

Ocean Front Suite with Direct Beach Access

Key West, Florida, United States

Summary:brbrSet on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West.brbrbrbrOn property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise.brbrbrbrDon’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.brbrbrbrThe Space:brbrWalk down from your private spiral staircase directly onto the sandy beach, where a stunning view of the Gulf of Mexico awaits.brbrSleeping arrangements include:brbrBedroom 1: King bed and en-suite bathroom with a double vanity and whirlpool tubbrbrLiving Area: Queen sleeper sofabrbrbrbrThe fully-equipped kitchen features stainless-steel appliances and includes all cooking essentials. With its open-concept floor plan, the indoor living area seamlessly connects to the private balcony, creating the perfect space for quality time.brbrbrbrGuest Access:brbrPersonalized check in experience!brbrOur luxury resort offers a heated pool, hot tub, on-site marina, restaurant and waterview fitness center.brbrGuests have access to a local Guest Experience Manager (GEM) for recommendations such as on-site bike rentals, water excursions, and our favorite places to eat.brbrbrbrThe Neighborhood:brbrConveniently located on north Key West, Beachside Resort sits on an ideal seven acres of land situated just 10 minutes from Duval Street, ensuring you can be as close or as far from the ‘happenings’ as you’d like. Our hotel contains over 200 guest rooms and suites, two on-property restaurants, a 46,000 gallon pool and Key West’s largest ballroom.brbrbrbrGetting Around:brbrParking Information:brbrGarage parking available on property for $25/night; with electric charging stations.brbrbrbrOn-site Shuttle & Rentals:brbrWe provide a daily shuttle from 9am to 11pm for easy access to Key West and its famed Duval Street attractions or check out our on-site bike & watercraft rentals at Brightwild Adventures.brbrbrbrOther Things to Note:brbr- Host your wedding, corporate, or social events in one of Key West's largest ballrooms with full in-house catering services available.brbr- This property is not pet-friendly.brbr- Private stackable washer/dryer.brbr- Parking is $25 per night, per vehicle plus tax.brbr- All housekeeping services are by request, additional fees may apply. No daily service provided.brbr- Primary guest must be 21 years old or older in order to reserve this property.

1

Bed

2

Bath

4

Sleeps

$298.36

/ Nightly

Condo

Poolside Suite with Direct Pool Access

Key West, Florida, United States

Summary:brbrExperience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in the perfect blend of adventure and relaxation in sunny Key West.brbrbrbrOn property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise.brbrbrbrDon’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.brbrbrbrThe Space:brbrStart each morning with direct access to our resort pool from your own pool view private balcony.brbrbrbrBedroom 1: King bed and en-suite bathroom with a double vanity and whirlpool tubbrbrLiving Area: Queen sleeper sofabrbrbrbrThe fully-equipped kitchen features stainless-steel appliances and includes all cooking essentials. With its open-concept floor plan, the indoor living area seamlessly connects to the private balcony, creating the perfect space for quality time.brbrbrbrGuest Access:brbrPersonalized check in experience!brbrOur luxury resort offers a heated pool, hot tub, on-site marina, restaurant and waterview fitness center.brbrGuests have access to a local Guest Experience Manager (GEM) for recommendations such as on-site bike rentals, water excursions, and our favorite places to eat.brbrbrbrThe Neighborhood:brbrConveniently located on north Key West, Beachside Resort sits on an ideal seven acres of land situated just 10 minutes from Duval Street, ensuring you can be as close or as far from the ‘happenings’ as you’d like. Our hotel contains over 200 guest rooms and suites, two on-property restaurants, a 46,000 gallon pool and Key West’s largest ballroom.brbrbrbrGetting Around:brbrParking Information:brbrGarage parking available on property for $25/night; with electric charging stations.brbrbrbrOn-site Shuttle & Rentals:brbrWe provide a daily shuttle from 9am to 11pm for easy access to Key West and its famed Duval Street attractions or check out our on-site bike & watercraft rentals at Brightwild Adventures.brbrbrbrOther Things to Note:brbr- Host your wedding, corporate, or social events in one of Key West's largest ballrooms with full in-house catering services available.brbr- This property is not pet-friendly.brbr- Private stackable washer/dryer.brbr- Parking is $25 per night, per vehicle plus tax.brbr- All housekeeping services are by request, additional fees may apply. No daily service provided.brbr- Primary guest must be 21 years old or older in order to reserve this property.

Bed

Bath

Sleeps

$297.62

/ Nightly

Condo

Pool View Suite | Beachside Resort

Key West, Florida, United States

Summary:brbrExperience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in the perfect blend of adventure and relaxation in sunny Key West.brbrbrbrOn property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise.brbrbrbrDon’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.brbrbrbrThe Space:brbrStart each morning with a view of our resort pool from your private balcony of this 1-bedroom condo, complete with a full kitchen, and washer/dryer.brbrSleeping arrangements include:brbrBedroom 1: King bed and en-suite bathroom with a double vanity and whirlpool tubbrbrLiving Area: Queen sleeper sofabrbrbrbrThe fully-equipped kitchen features stainless-steel appliances and includes all cooking essentials. With its open-concept floor plan, the indoor living area seamlessly connects to the private balcony, creating the perfect space for quality time.brbrbrbrGuest Access:brbrPersonalized check in experience!brbrOur luxury resort offers a heated pool, hot tub, on-site marina, restaurant and waterview fitness center.brbrGuests have access to a local Guest Experience Manager (GEM) for recommendations such as on-site bike rentals, water excursions, and our favorite places to eat.brbrbrbrThe Neighborhood:brbrConveniently located on north Key West, Beachside Resort sits on an ideal seven acres of land situated just 10 minutes from Duval Street, ensuring you can be as close or as far from the ‘happenings’ as you’d like. Our hotel contains over 200 guest rooms and suites, two on-property restaurants, a 46,000 gallon pool and Key West’s largest ballroom.brbrbrbrGetting Around:brbrParking Information:brbrGarage parking available on property for $25/night; with electric charging stations.brbrbrbrOn-site Shuttle & Rentals:brbrWe provide a daily shuttle from 9am to 11pm for easy access to Key West and its famed Duval Street attractions or check out our on-site bike & watercraft rentals at Brightwild Adventures.brbrbrbrOther Things to Note:brbr- Host your wedding, corporate, or social events in one of Key West's largest ballrooms with full in-house catering services available.brbr- This property is not pet-friendly.brbr- Private stackable washer/dryer.brbr- Parking is $25 per night, per vehicle plus tax.brbr- All housekeeping services are by request, additional fees may apply. No daily service provided.brbr- Primary guest must be 21 years old or older in order to reserve this property.

1

Bed

2

Bath

4

Sleeps

$984.26

/ Nightly

Condo

Ocean Front Presidential Suite | Beachside Resort

Key West, Florida, United States

Summary:brbrSet on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West.brbrbrbrOn property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise.brbrbrbrDon’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.brbrbrbrThe Space:brbrOur three-bedroom, three-bathroom condo provides everything you need for your next getaway to Beachside Key West.brbrbrbrSleeping arrangements include:brbrBedroom 1: King bed and en-suite bathroom with a double vanity and whirlpool tubbrbrBedroom 2: King bed with en-suite bathroom brbrBedroom 3: Two twins brbrLiving Area: Queen sleeper sofabrbrbrbrThe fully-equipped kitchen features stainless-steel appliances and includes all cooking essentials. With its open-concept floor plan, the indoor living area seamlessly connects to the private balcony, creating the perfect space for quality time.brbrbrbrGuest Access:brbrPersonalized check in experience!brbrOur luxury resort offers a heated pool, hot tub, on-site marina, restaurant and waterview fitness center.brbrGuests have access to a local Guest Experience Manager (GEM) for recommendations such as on-site bike rentals, water excursions, and our favorite places to eat.brbrbrbrThe Neighborhood:brbrConveniently located on north Key West, Beachside Resort sits on an ideal seven acres of land situated just 10 minutes from Duval Street, ensuring you can be as close or as far from the ‘happenings’ as you’d like. Our hotel contains over 200 guest rooms and suites, two on-property restaurants, a 46,000 gallon pool and Key West’s largest ballroom.brbrbrbrGetting Around:brbrParking Information:brbrGarage parking available on property for $25/night; with electric charging stations.brbrbrbrOn-site Shuttle & Rentals:brbrWe provide a daily shuttle from 9am to 11pm for easy access to Key West and its famed Duval Street attractions or check out our on-site bike & watercraft rentals at Brightwild Adventures.brbrbrbrOther Things to Note:brbr- Host your wedding, corporate, or social events in one of Key West's largest ballrooms with full in-house catering services available.brbr- This property is not pet-friendly.brbr- Private stackable washer/dryer.brbr- Parking is $25 per night, per vehicle plus tax.brbr- All housekeeping services are by request, additional fees may apply. No daily service provided.brbr- Primary Guest must be at least 21 years of age or older in order to reserve this property.

3

Bed

3

Bath

8

Sleeps

$617.81

/ Nightly

Condo

Ocean Front Two Bedroom Residence

Key West, Florida, United States

Summary:brbrSet on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West.brbrbrbrOn property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise.brbrbrbrDon’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.brbrbrbrThe Space:brbrStart each morning overlooking the Gulf of Mexico from your private balcony of this 2-bedroom condo, complete with everything you need for your Beachside escape.brbrbrbrSleeping arrangements include:brbrBedroom 1: King bed and en-suite bathroom with a double vanity and whirlpool tubbrbrBedroom 2: King bed with en-suite bathroom (separated via lock out door)brbrLiving Area: Queen sleeper sofabrbrbrbrThe fully-equipped kitchen features stainless-steel appliances and includes all cooking essentials. With its open-concept floor plan, the indoor living area seamlessly connects to the private balcony, creating the perfect space for quality time.brbrbrbrGuest Access:brbrPersonalized check in experience!brbrOur luxury resort offers a heated pool, hot tub, on-site marina, restaurant and waterview fitness center.brbrGuests have access to a local Guest Experience Manager (GEM) for recommendations such as on-site bike rentals, water excursions, and our favorite places to eat.brbrbrbrThe Neighborhood:brbrConveniently located on north Key West, Beachside Resort sits on an ideal seven acres of land situated just 10 minutes from Duval Street, ensuring you can be as close or as far from the ‘happenings’ as you’d like. Our hotel contains over 200 guest rooms and suites, two on-property restaurants, a 46,000 gallon pool and Key West’s largest ballroom.brbrbrbrGetting Around:brbrParking Information:brbrGarage parking available on property for $25/night; with electric charging stations.brbrbrbrOn-site Shuttle & Rentals:brbrWe provide a daily shuttle from 9am to 11pm for easy access to Key West and its famed Duval Street attractions or check out our on-site bike & watercraft rentals at Brightwild Adventures.brbrbrbrOther Things to Note:brbr- Host your wedding, corporate, or social events in one of Key West's largest ballrooms with full in-house catering services available.brbr- This property is not pet-friendly.brbr- Private stackable washer/dryer.brbr- Parking is $25 per night, per vehicle plus tax.brbr- All housekeeping services are by request, additional fees may apply. No daily service provided.brbr- Primary Guest must be at least 21 years of age or older in order to reserve this property.

2

Bed

2

Bath

6

Sleeps

$630.98

/ Nightly

Condo

Pool View 3BR Residence | Beachside Resort

Key West, Florida, United States

Summary:brbrSet on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West.brbrbrbrOn property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise.brbrbrbrDon’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.brbrbrbrThe Space:brbrWake up to a scenic resort pool view from the private balcony of this expansive 3-bedroom condo. As our largest accommodation on the property, it's fully equipped for your next Beachside Key West getaway.brbrbrbrSleeping arrangements include:brbrBedroom 1: King bed and en-suite bathroom with a double vanity and whirlpool tubbrbrBedroom 2: King bed with en-suite bathroom brbrBedroom 3: Two twins brbrLiving Area: Queen sleeper sofabrbrbrbrThe fully-equipped kitchen features stainless-steel appliances and includes all cooking essentials. With its open-concept floor plan, the indoor living area seamlessly connects to the private balcony, creating the perfect space for quality time.brbrbrbrGuest Access:brbrPersonalized check in experience!brbrOur luxury resort offers a heated pool, hot tub, on-site marina, restaurant and waterview fitness center.brbrGuests have access to a local Guest Experience Manager (GEM) for recommendations such as on-site bike rentals, water excursions, and our favorite places to eat.brbrbrbrThe Neighborhood:brbrConveniently located on north Key West, Beachside Resort sits on an ideal seven acres of land situated just 10 minutes from Duval Street, ensuring you can be as close or as far from the ‘happenings’ as you’d like. Our hotel contains over 200 guest rooms and suites, two on-property restaurants, a 46,000 gallon pool and Key West’s largest ballroom.brbrbrbrGetting Around:brbrParking Information:brbrGarage parking available on property for $25/night; with electric charging stations.brbrbrbrOn-site Shuttle & Rentals:brbrWe provide a daily shuttle from 9am to 11pm for easy access to Key West and its famed Duval Street attractions or check out our on-site bike & watercraft rentals at Brightwild Adventures.brbrbrbrOther Things to Note:brbr- Host your wedding, corporate, or social events in one of Key West's largest ballrooms with full in-house catering services available.brbr- This property is not pet-friendly.brbr- Private stackable washer/dryer.brbr- Parking is $25 per night, per vehicle plus tax.brbr- All housekeeping services are by request, additional fees may apply. No daily service provided.brbr- Primary Guest must be at least 21 years of age or older in order to reserve this property.

Bed

Bath

Sleeps

$695.54

/ Nightly

Condo

**TOP OF OLD TOWN @ DUVAL SQUARE** Renovated Home + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrPerched above the sights and sounds of Duval Street, sits TOP OF OLD TOWN, a recently renovated 2-bedroom private home, located within a secluded community in the heart of Old Town. This hidden gem offers a spacious interior, multiple outdoor spaces, and access to the community pool. Combined with Last Key Realty’s Five Star Guest Services & Complimentary Concierge, your stay at TOP OF OLD TOWN will leave you feeling on top of the world.brbrTHE LOCATION & COMMUNITY...brbrTOP OF OLD TOWN is located in the Duval Square community, with entrances from Duval, Virginia, and Simonton Streets. This location means you'll enjoy the convenience of having shops, restaurants, and art galleries right at your doorstep. Take a refreshing dip in the beautiful community pool or unwind in the spacious common area overlooking the bustling street below.brbrNo visit to Key West would be complete without a selfie at the iconic Southernmost Point Buoy, which is located just a few blocks away. You’ll also be within walking distance to several of Key West's best and most unique restaurants, including Martin’s, Moondog Cafe and 915. While you won't need a car to get around, this condo does include one covered, off-street parking space in the parking garage.brbrTHE LIVING AREA...brbrStep inside and be greeted by a bright and airy, open concept living space. Relax on the plush sofa, which converts to a queen sleeper for extra guests, and enjoy your favorite shows on the large flat-screen TV. The adjacent dining area comfortably seats six, perfect for gathering with friends and family.brbrThe fully equipped kitchen is a chef's dream, featuring new luxury appliances and all the essentials you need to whip up delicious meals. Prefer to dine al fresco Step out onto your private covered balcony and savor your meal while soaking up the lively atmosphere of Duval Street.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom - Located on the Second Floor with a King bed, flat-screen TV, full closet, balcony access and an en-suite bathroom with a walk-in shower.brbr** Guest Bedroom - Located on the Second Floor with a King bed, flat-screen TV, full closet, and an en-suite bathroom with a walk-in shower.brbr** The Living Area sofa pulls out to a Queen-size bed.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TV in Living Roombr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & Cable TV includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked condo also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Assigned off-street carport for 1 carbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Pets Not Allowedbr** No Smoking Allowed - not even on the porchbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

Bed

Bath

Sleeps

$221.52

/ Nightly

Condo

J Ferrara #9: Charming Studio Oasis, Steps from Duval Street, Southernmost Point & Shared Pool!

Key West, Florida, United States

Welcome to J Ferrara, your ideal retreat in the heart of Key West! brbr brbrNestled on a quiet street in the artist-inspired condominium complex in Bahama Village, The Galleria has a rich history dating back to the early 1900s. It was once a popular spot for traveling artists who came to Key West for inspiration and showcased their work in the nearby art galleries on Duval Street. Our cozy studio offers a peaceful base for your fun, adventurous vacation. Just 10 blocks from the beach & a short 2.5 blocks from the famous Duval Street, our location provides easy access to the best of Key West. Whether you're returning from a day of sun & sand, a boat excursion, or a leisurely stroll down Duval Street, our studio is the perfect Old Town Key West stay! Our vacation rental is named after one of our dear and talented friends, James Ferrara of J Ferrara Gallery. Based in South Florida, James specializes in underwater photography. You will find several of his pieces throughout the room! Whether you seek relaxation, adventure, or a mix of both, J Ferrara provides the perfect base for your Key West getaway. brbr brbrSLEEPS MAXIMUM OF 2 GUESTS: brbr brbrBedroom: Queen Bed, Smart TV (no cable/satellite TV) brbr brbrKitchenette: Lightly Equipped (dorm size refrigerator/freezer, sink, microwave, Keurig, drip coffee maker) brbr brbrAMENITIES: brbr brbr- Shared Heated (Nov-Apr) Pool brbr brbr- Shared Laundry brbr brbr- Shared Bike Rack brbr brbr- Shared Propane BBQ Grill & Picnic Area brbr brbr- Keurig & Drip Coffee Maker brbr brbr- Linen's and Bath/Pool Towels Provided brbr brbr- Street Parking available, no off-street/designated parking available brbr brbr- 2.5 blocks to Duval Street brbr brbr- 0.4 miles to Southernmost Point brbr brbr- 0.7 miles to Fort Zachary Taylor State Park/Beach brbr brbr- 1.1 miles to Mallory Square Sunset Pier brbr brbr- 1.2 miles to Key West Historic Seaport brbr brbr- 2.6 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrUnit Size: Please be aware, this unit is a cozy 138 sq. ft. studio—while compact, it provides all the essentials for a comfortable and enjoyable stay. brbr brbrAge and Occupancy Requirements: Booking tenant must be 25 years of age or older and must occupy the property for the entire duration of the booking. Furthermore, this property is exclusively available as a vacation rental and is not available for worker housing. brbr brbrNo Smoking: Smoking is strictly prohibited within the property to maintain a smoke-free environment for all guests. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of guests and property, exterior security cameras monitor all exterior areas of the complex. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

1

Bath

2

Sleeps

$337.5

/ Nightly

Condo

Downtown Sunset Harbor Studio!

Key West, Florida, United States

This is a great studio unit at Hyatt Sunset Harbor in downtown Key West. Walk along the boardwalk or head to Duval Street only a couple blocks away. The resort has pool, hot tub, and grills for use during your stay.brbrThere are laundry facilities on site free of charge. There are NO daily resort fees, but parking is extra.brbrEach unit has a King sized bed, kitchenette with microwave and mini fridge, and bathroom.brbrWeeks are Sun-Sun.

Bed

Bath

Sleeps

$529.81

/ Nightly

Condo

Truman Annex Best Location in Town

Key West, Florida, United States

We stick to a Saturday check in during the in season months (Jan-April)brbrGreetings from Paradise, where the temperature is 82 degrees, water temperature 80, and the wind SE at 10, just enough breeze to blow sand in my margarita.brbr'Margarita Villas' are located in historic Old Town in a beautiful, very private gated compound that has won awards as the best development in Florida. (And yes it does have a blender).brbrIt’s just off Duval Street, with its bustling shops and nightlife; yet quiet and private. Fort Zachary Taylor on the south side of the property has one of our most picturesque beaches located among the tall whispering pines of the uplands; the view of the reef and the turquoise waters is magnificent.brbrThe heated pool is conveniently located nearby so you are never far from a refreshing dip or just 'conching out' in the sun.brbrThere are two bedrooms and one baths; the master bedroom is furnished with a queen-size bed, the other, two twins. French doors in the living room open onto the garden deck for outdoor dining or to catch the tropical breezes. Outdoor porch furniture on the deck.brbrThe kitchen is completely equipped (including the mandatory BLENDER).brbrFully air-conditioned, all rooms have tropical ceiling fans and all linens are provided. There is off street parking for one car.brbr brMike WernicoffbrbrPS: Did I mention that we have a BLENDER brbrKeywords: Condominiumbr

2

Bed

1

Bath

4

Sleeps

$299.03

/ Nightly

Condo

Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews

Key West, Florida, United States

If you are looking to stay in accommodations of high standards. This is the one for you! As you enter this large one bedroom condo you are greeted with a beautiful view the Atlantic Ocean. Completely upgraded with all new furniture and large flat screen televisions. The kitchen is upgraded and room for two chefs. The master bedroom has a king bed and en suite bathroom with large flat screen television. Top of the line queen sleeper for your guests and an indoor dinning room table set for those special meals. Relax from your private balcony that overlooks the ocean and one of Key West largest beaches or enjoy the large resort-style community pool with Jacuzzi. There is a bbq grill area for your use as well as a tennis court. Free wi-fi and free covered parking bay. brDon't miss this one...book today!brbrNote: The property is set up for no contact check-in. The unit has been cleaned and sanitized by a professional cleaning company prior to your arrival. If Key West closes to tourists due to COVID related travel shutdown, you will recieve 100% refund minus credit card fee of 3.5%.

1

Bed

1

Bath

2

Sleeps

$308.2

/ Nightly

Condo

The Cat Island Suite | Charmingly Renovated w/ Pool

Key West, Florida, United States

The Cat Island Suite | Updated! Stunning Sunset View, Pool!brbrEscape to The Cat Island Suite, a serene, beautifully updated, and well-appointed 2-bedroom condo located in the peaceful Sunrise Suites community on the east side of Key West. Just a mile from the beach, this charming getaway provides the perfect combination of relaxation and adventure. Whether you're lounging by the pool, exploring nearby attractions, or enjoying the comfort of your condo, The Cat Island Suite is the ideal place to unwind and create lasting memories.brbrThe Ambiance:brStep into The Cat Island Suite and experience a delightful blend of modern tropical charm. This stylish condo features luxurious finishes and an open-concept kitchen and living room layout that's perfect for gathering with family or friends. The two-bedroom suite accommodates up to four guests, offering:brbr- King-sized bed in the primary bedroombr- Queen-sized bed in the second bedroombrbrThe primary bedroom features a beautiful ensuite bathroom complete with modern walk-in shower, perfect for that spa-like feel. The fully equipped kitchen makes preparing meals a breeze, whether you're brewing your morning coffee with the Keurig or cooking on the electric stove. Relax on your private balcony and take in the views, or enjoy TV, WiFi, and central air conditioning for added comfort.brbrGuest Access:brEnjoy a seamless arrival with our contactless check-in process, where you'll receive a personalized access code to enter your unit. During your stay, make the most of the shared amenities, including:brbr- Shared heated pool and hot tubbr- Tennis courtbr- Walking paths and biking trailsbrbrLocation Highlights:brThe Cat Island Suite is ideally located within the peaceful Sunrise Suites Resort, just a short distance from Key West's best attractions. A quick 10-minute drive takes you to the lively Duval Street, where you'll find a vibrant selection of restaurants, bars, and entertainment. The Key West Airport is also just a short drive away, making travel easy and stress-free.brbrGetting Around: brWith parking available, you'll have convenient access to explore the island by car. For those who prefer to travel by bike, scooter, or golf cart, rentals are available nearby. Key West's walkability means many attractions are just a short stroll away, and for longer distances, taxis and rideshare services are readily available.brbrOther Things to Note:br- The pool and hot tub are shared with other guests of the complex.br- No pets allowed in this unit.br- Private washer/dryer in unit.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, pool, parking areas, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

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Sleeps

$286.6

/ Nightly

Condo

Sunrise 308-2BR/2BA condo near beaches with pool, parking, balcony

Key West, Florida, United States

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrFEATURES:brBedrooms: 2 (1 king, 1 queen, sofa sleeper recommended for children ONLY)brBathrooms: 2 brLocation: Sunrise SuitesbrSquare Feet: 798brParking: 2 parking spaces includedbrAmenities: Wifi, TVs, in-unit laundry, shared pool, close to beaches, private balconybrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

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$160.47

/ Nightly

Condo

Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach Beach.

Key West, Florida, United States

This condo has a unique location in the Gated Truman Annex. It is very quiet, but yet very close to all Key West has to offer. brThe entrance road to the Ft Zachary Taylor St. Beach Park is right at the end of our block, for Lazy Days of snorkeling, swimming and sightseeing. The best sunset spot.brDuval St. is 2 blocks up, with shopping, restaurants and world class entertainment.brThe 2 porches, for privacy and sun options, also separates this from other properties.brWe also have a heated pool just across the courtyard.brThe 2 old town harbors, are also close by for all you ocean adventures, or just sightseeing.brbrbrKeywords: Key West, Truman Annex, 1/2 block from new Waterfront Park, Ft Zach Beach Access, Heated Pool, 2 porches, 2 bedrooms, washer/Dryer, dishwasher, 43' smart TV, 2 blocks to Duval and Mallory sq., 1 block to Green Parrot and Truman White House, Private Security, Parking, A/C, WiFi, Linens and cookware. Quiet.

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Sleeps

$703.13

/ Nightly

Condo

OCEAN MEMORIES CONDO- 2 Bedroom, 2 Bath Oceanfront w/ Pool & Hot Tub

Key West, Florida, United States

br*Oceanfront Escape with Breathtaking Views – Steps from the Marina*brbrAwaken each morning to breathtaking sunrises stretching across the vast Atlantic, visible without even leaving the comfort of your bed. Nestled in tranquil Key West, this idyllic retreat boasts sweeping, uninterrupted ocean views and a private balcony that invites you to savor your morning coffee while soaking in the sights and sounds of nature. Watch graceful pelicans glide overhead, and enjoy peaceful moments of birdwatching as the day begins.brbr*THE Ideal Location for Adventure & Relaxation*brbrJust a short walk from a world-class marina, enjoy the vibrant energy of the island as fishing boats return with the day’s catch. Watch as captains clean their fish and feed the waiting tarpon—or join in! Hand-feed the tarpon yourself, pick up fresh seafood, and grill it poolside for a memorable meal under the palms.brbrLooking to get out on the water Book a charter with Captain Brad aboard Southpaw, a 43’ sportfishing boat renowned for unforgettable excursions.brbr*Unwind with Sunset Views & Local Flavors*brbrAs evening falls, wind down with a drink on the balcony while cruise ships glide into Key West Harbor and the sky lights up with sunset hues. Ready for dinner Take a short stroll to Yellowfin Bar & Grill for fresh-caught seafood and laid-back island vibes.brbr*Gorgeous 2-Bedroom, 2-Bath Stock Island Condo w/Private Pool & Hot Tub*brbrWhen you're ready to explore, downtown Key West is just 10 minutes away. Dive into activities like snorkeling, sunset cruises, or day trips to Dry Tortugas National Park. Don’t miss the famous Sunset Celebration at Mallory Square, where magicians, street performers, and live entertainment create a lively, memorable atmosphere that'll not fail to heighten your vacation experience.brbrVery welcoming, very clean, well stocked, and had a beautiful view. ~guest, Kim M.brbrOcean Memories Condo is located directly on the Atlantic with stunning ocean views from the kitchen, living room, master bedroom, and bathroom - as well as from the comfort of your own private balcony (a guest favorite)! The condo is furnished with comfortable, high-end furniture and impressive décor. The unit is fully equipped with state-of-the-art appliances, dishes, washer/dryer, and Wi-Fi. Approx. 1800 Sq. Ft. brbr**Be sure to check out our 5-star reviews**brbrNOTE: to see all photos use the and widgets abovebrbr***********************************************************br---- PARKING: Each unit comes with covered assigned parking.br---- GROUPS OF 5-6: This condo is best suited for groups of 4 or lessbr***********************************************************brbrbrbrkeywords: ocean's edge marina, condominium, condo, 2-bedroom, two-bedroom, two bedroom, oceanfront, key west, stock islandbrbr**Owner is available by phone 24 hours a day to answer any questions or address any concerns.**

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Sleeps

$442.45

/ Nightly

Condo

Key West Oceanfront Condo - 'The Sea Jay'

Key West, Florida, United States

The condo is quite large at over 1150 square feet and looks directly at beautiful Smathers Beach. The 'Sea Jay' is located in La Brisa which is a gated community. It features a very large master bedroom with dressing room and a full bathroom. We look out at the beautiful Atlantic Ocean from the master bedroom, balcony and living room. Adjacent to the beach is Key West's longest sidewalk along the ocean for bike riding, jogging or walking. La Brisa has a heated pool, jacuzzi, sauna, clubhouse, lighted tennis court, three BBQ grills, picnic benches and covered Tiki huts. It is a quiet, family friendly location surrounded by tropical foliage. Consider us your 4 star luxury hotel suite but with the advantage of your own kitchen and a large second bedroom with another full bathroom. The condo has central A/C, cable TV in each room and a washer/dryer with all the conveniences of home in a secure setting. La Brisa is on the edge of old and new town in beautiful Key West.brbrbrKey West is easy to find and you can't get lost! Starting at the Miami International Airport or simply driving down from the north, you only need to get on U.S. Hwy. 1 and go south. The drive is just beautiful as the keys are linked by 42 bridges including the spectacular 7 mile bridge with outstanding water views all the way. The mile markers will tell you how far you have come.brbrKey West is located approximately 160 miles south of Miami and is about a 3 1/2 hour drive.brbrYou can also fly directly into Key West Airport and we are located only one mile away.brbrNOTE: No RV’s or Camping Trailers.

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$622.5

/ Nightly

Condo

Gated Parking, Heated Pool - Villa Positano

Key West, Florida, United States

Summary:br- Centralized in the middle of Duval Street & walking distance to popular activities!br- Duval Square two bedroom two & half bath condo.br- On the intersection of Truman Avenue and Duval Street, just a 10 minute walk to downtown bars, restaurant and attractions.br- Off-street parking & rooftop pool access overlooking Duval Street.brbrThe Space:brVilla Positano features a private deck and open-concept kitchen perfect for entertaining and quality time with loved ones. brbrBedroom 1: Primary bedroom with king bed, vaulted ceilings, en suite bathroom and balcony.brBedroom 2: Queen bed with en suite bathroom.brExtra Sleeping: Queen sofa sleeper in the living area. brbrThe Duval Square complex is home to popular restaurants and shops. Located above you will find the small condo community featuring a rooftop pool and tropical landscaping.brbrGuest Access:brOur self check-in makes the process seamless. brbrGuests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrThe Neighborhood:brOn the 1000 Block of Duval Street located in Duval Square this second story condo is in close proximity all of your Key West favorites. Explore local restaurants directly below the complex, such as New York Pasta Garden and Origami Sushi or make your way to Duval Street for art galleries, more food, shopping and nightlife. Villa Positano is also walking distance to the Southernmost Point!brbrGetting Around:brOff-street parking provided for 1 vehicle.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi or by feet. This unit is located in downtown Key West and many attractions are within walking distance. Feel free to ask us for recommendations!brbrOther Things to Note:br-This unit features a private stackable washer/dryer.br- This unit is not pet friendly.br- Unit is located on the second floor with both stair & elevator access.

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Sleeps

$626.94

/ Nightly

Condo

Heated Rooftop Pool, Gated Parking - Casa Caribe

Key West, Florida, United States

Summary:br- Located on the quiet end of Duval Street steps from the Southernmost Point!br- Spacious two-story townhouse in Duval Square condominium complex.br- On the intersection of Truman Avenue and Duval Street, just a 10 minute walk to downtown bars, restaurants and attractions.br- Off-street parking & rooftop pool access overlooking Duval Street.brbrThe Space:brCasa Caribe features a private deck and open-concept kitchen perfect for entertaining and quality time with loved ones. brbrBedroom 1: Primary bedroom with king bed, vaulted ceilings, en suite bathroom and balcony.brBedroom 2: Queen bed with en suite bathroom.brExtra Sleeping: Queen sofa sleeper in the living area. brbrEnjoy the Duval Square complex home to restaurants and shops right on Duval street. A shared rooftop pool with lounge chairs is located on the rooftop.brbrGuest Access:brOur self check-in makes the process seamless. brbrGuests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrThe Neighborhood:brOn the 1000 Block of Duval Street located in Duval Square this second story condo is in close proximity all of your Key West favorites. Explore local restaurants directly below the complex, such as New York Pasta Garden and Origami Sushi or make your way to Duval Street for art galleries, more food, shopping and nightlife. Casa Caribe also walking distance to the Southernmost Point!brbrGetting Around:brOff-street parking for 1 vehicle included with your stay.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi or by feet. This unit is located in downtown Key West and many attractions are within walking distance. Feel free to ask us for recommendations!brbrOther Things to Note:br-This unit features a private stackable washer/dryer.br- This unit is not pet friendly.br- Unit is located on the second floor with both stair & elevator access.

2

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2

Bath

6

Sleeps

$639.75

/ Nightly

Condo

Penthouse Beach Ocean Views- Live the Dream

Key West, Florida, United States

brYou feel the excitement the moment you arrive. The warm tropical breezes, the blue green water. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grace of Key West in a new and distinctive setting. We hope that you will enjoy staying directly on the ocean and enjoy the beautiful views and you will agree that Excitement has been found. Enjoy this upgraded two-bedroom, two-bath condominium with 1350 square feet of living space. Enjoy ocean views and the colors of the sunset from your private 35-foot balcony. brMaster bedroom has comfortable king-size bed; Second bedroom with Comfortable Queen & Twin . Queen sleeper sofa is in the living room Every room has high speed private WiFi. br Key West Luxury Living at it's best. Resort Swimming Pool , Bubbling hot tub, Sauna and Gym are complimentary for our guests Several picnic and barbecue areas surrounded by the native tropical gardens add to our guest options. Water sports, Snorkeling and the Coral Reef are all available at Smathers Beach which is steps away . EXCITEMENT ON THE KEY WEST OCEAN Our other VRBO Listings #4091149 & #154612brbrWE WILL BE TRANSITIONING OUR VRBO ACCOUNT TO ALL FLORIDA KEYS BASED IN KEY WEST. ALL BOOKINGS FROM JULY 1ST 2026 WILL GO THROUGH ALL FLORIDA KEYS. VRBO #20282915.

2

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2

Bath

6

Sleeps

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