Pet Friendly Vacation Rentals Deals in Florida Keys & Key West

Key Largo Private vacation home - 5.0 Star Review

Jacuzzi to die for w/BBQ, fire pit, and plenty of room to enjoy. Near restaurants, clubs, bars, the ocean, and John Pennekamp park for scuba diving. Near by parasailing and water sports available.!!!!.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Cudjoe Key Private vacation home

The 3 bedroom 2 bath home is immaculate. Private heated and chilled pool. Concrete seawall for your 35' boat. Deep water and easy access out to the open waters.
This home has a minimum night stay of 28 nights. There is ample outdoor living space that includes lounge chairs, outdoor furniture BBQ Grill and dining table. There are 2 kayaks fo.......read more

3 Bedroom(s)
Sleeps 7
Private vacation home

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Islamorada Private vacation home

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

Studio
Sleeps 4
Private vacation home

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Key Largo Mobile home

Your home away from home in the Florida Keys! Our 3 bedroom Guest House is located on the Oceanside of Key Largo in a friendly and quiet neighborhood, 2 Minutes from Oceanside and boat ramp is within the community. 42 FT Dock available at property. 2 person Kayak available at property to stroll around ocean nature. Five to ten minutes from great fi.......read more

4 Bedroom(s)
Sleeps 7
Mobile home

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Key Largo Private vacation home

Get Ready to be amazed with this beautiful home! As you walk in, you'll be welcomed by the best panoramic view of the Keys. You can see plenty marine life right from your deck, and even catch some fish. Got a boat? Perfect, the best of the boating capital of the world awaits. Or relax on the pool with a million dollar view. Get comfortable with top.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Key largo Mobile home - 4.9 Star Review

Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds, and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards.

10 Min Drive to the Gilber.......read more

3 Bedroom(s)
Sleeps 6
Mobile home

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Summerland Key Private vacation home

Completely remodeled, high-end Summerland Key home! Meticulously designed vacation property with exquisite furnishings throughout the home, quartz countertops, and top-of-the-line stainless steel appliances. This newly remodeled home has a lovely open & entertaining feel to the living, dining, and large outdoor spaces! The home consists of four la.......read more

4 Bedroom(s)
Sleeps 14
Private vacation home

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Key West Private vacation home - 4.8 Star Review

Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay at this Island Chic property is filled with luxury and personalized touches. A home designed by a local and prestigious architect, amenities here offer a fully bountiful experience of extravagance that will make any visitor feel li.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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marathon Private vacation home - 5.0 Star Review

VACA-23-42 Romantic villa that is your ideal home away from home with a private saltwater pool on the waterfront. Sit out on the dock and you will see manatees and other wildlife. It is centrally located to popular restaurants and exciting attractions for all ages and a short boat ride to the gulf or the ocean, you can also drive your boat right to.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Little Torch Key Private vacation home - 5.0 Star Review

Welcome to Paradise!
Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Haven House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring.......read more

4 Bedroom(s)
Sleeps 10
Private vacation home

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Key West Apartment

Summary:
- The historic James House sits on Caroline street, just one home away from Duval street and its coveted attractions, top-tier dining and nightlife.
- Included with your stay, across the street you can self-tour and enjoy the pool at the iconic Curry Mansion built in 1869. The mansion houses a collection of unique architectural detai.......read more

Studio
Sleeps 4
Apartment

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Key West Private vacation home

Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few minutes walk to several local attractions. An onsite restaurant serves Latin-inspired tapas with local ingredients. The refreshing pool and pool bar are a relaxing spot to spend an afternoon in the sun. Hourly shuttle services are.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Key Largo Private vacation home - 5.0 Star Review

This ocean and canal front property comes with beautiful panoramic ocean views from the pool or wrap around upper deck. Located in a secluded nature preserve, making this the perfect place for relaxation, contemplation and meditation. While still only a 10 miles to either downtown Key Largo, or to Ocean Reef Club.
Take a dip in the ocean, bri.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Key West Private vacation home - 4.8 Star Review

BEGIN YOUR ISLAND ESCAPE...
Come get lost in the magic of this captivating island retreat offering modern amenities within this old-world, historic setting. Savor sweet moments with your loved ones while enjoying a simple agenda, lounging indoors or tooling around town by foot to all the highly sought-after Key West attractions.
***PRIMARY G.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Summerland Key Private vacation home - 4.5 Star Review

Welcome to "Anchors Aweigh," your passport to the ultimate oceanfront retreat on the tranquil shores of Summerland Key. This charming open water home offers a unique opportunity with two distinct living areas, tailor-made for two families or your cherished extended family. Set against the backdrop of the setting sun, you'll unwind with your toes bu.......read more

3 Bedroom(s)
Sleeps 12
Private vacation home

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Ramrod Key Private vacation home

Mermaid House was just recently renovated and is a brand new second level vacation rental! This home is in a great central location, not far from Winn-Dixie, Bahia Honda State Park, and Key West!
Decorated with a coastal feel, this home has an open floor plan! The home is a corner of a canal and has 30' of dockage on one side & 20' on the other .......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Private vacation home

BEDAZZLING COMPOUND...
Two delightful conch style island homes are situated on one glorious parcel in Old Town, just a stone's throw away from the magic of Duval Street and the historic Seaport. Each home features 3 bedrooms with private bathrooms, as well as their own sparkling heated pools. Quintessential Key West charm abounds and captures yo.......read more

6 Bedroom(s)
Sleeps 16
Private vacation home

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Summerland Key Private vacation home - 5.0 Star Review

Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property....two cottages (each two-bedroom) and a main house overlooking the ocean. Located between the houses is a breathtaking resort-style pool, diving pool, and hot tub.

Minimum 28-day rental. NO, this is NOT available to rent.......read more

7 Bedroom(s)
Sleeps 14
Private vacation home

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Islamorada Private vacation home

Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-park.......read more

3 Bedroom(s)
Sleeps 12
Private vacation home

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Key Largo Private vacation home

Water front upstairs Duplex with 50 feet of deep water Dockage ,minutes from open Ocean.
Comfortable 3 bedroom 2 bath house completely renovated, centrally located in prestigious Port Largo Neighborhood, minutes from all water activities imaginable.
Enjoy Deep Sea Fishing, Snorkeling, Spear Fishing, Kayaking and much more. World known Joh.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Cudjoe Key Private vacation home - 4.7 Star Review

Shangri-la in the Keys! Enjoy the water views and a 45' dock space!
VO unit 413 - 2Bd/2Ba Stilt Home
New to the rental program this beautiful stilted 2Bd/2Ba furnished vacation home features an oversized 45' concrete seawall perfect for those with larger boats! The dock amenities include dock posts, cleats, swim ladder, outdoor shower, wat.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Duck Key Private vacation home - 4.0 Star Review

This home is a 28 day minimum only.
You must be 25 or older to rent. (25 year old must be present during entire stay)

Your Coastal Sheek Duck Key Getaway! Beautifully appointed home with Open Floor plan.   Cathedral ceilings and views from every room of the ocean.  The house has a huge yard for privacy, and a swimming pool and Tiki Hut, p.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Summerland Key Private vacation home

Lower Keys Living at its very best. This This Modern 1,700 sq ft Old Florida Keys Waterfront House is located on Lower Sugarloaf Shores at Mile Marker 17, a half mile off of US 1 in an extremely quiet neighborhood and is available for 28+ day rentals. It is a three bedroom, three baths elevated house. All of the bedrooms are located on the second .......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Key West Private vacation home

Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the newly built property. Each unit features 2 Queen beds and accommodates 4 guests. The p.......read more

3 Bedroom(s)
Sleeps 12
Private vacation home

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Key West Private vacation home

Welcome to the Cottage On Newton, where you can experience the authentic Key West lifestyle in this newly updated Conch House. Nestled in the peaceful neighborhood of The Meadows, you'll find yourself in the quieter side of town, yet conveniently close enough to explore the vibrant attractions. Immerse yourself in the local way of life by residing .......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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Key West Private vacation home - 4.7 Star Review

Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the newly built property.

PLEASE NOTE:
- The resort fee is not included in the d.......read more

Studio
Sleeps 2
Private vacation home

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Marathon Private vacation home - 4.9 Star Review

*** This property is completely renovated on the inside and out! We cordially invite you to our property and enjoy the vacations that you really want! ***

Welcome to Duck Key Vacation Rentals! Located on a private island in the Florida Keys, our Villa is the perfect spot for your next vacation! Within walking distance, you’re only minutes aw.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Marathon Private vacation home - 4.0 Star Review

The Manatee Bay has the best of all worlds. It has a large custom fiberglass pool situated next to a 20 ft+ deep and beautiful swim able and fish-able lagoon. The Lagoon is filled with all sorts of different wildlife, including an occasional manatee, turtles, and all sorts of fish. It is the perfect place to learn to Paddle Board, Snorkel, or Ka.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Islamorada Private vacation home - 4.9 Star Review

Key Lime Villa #3 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of the Art District of Islamorada. Key Lime Villa #3 offers three bedroom/three and a half baths and is fully furnished, has private decks with water/sunset views right on the bay! Guests can enjoy the property’s bayside boat dock .......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Key Largo Apartment

*28 day minimum** Private 1 bedroom 1 bathroom apartment on beautiful canal. This cozy unit features a full kitchen, wireless internet, and cable TV. Patio overlooking a beautiful canal that leads out to open water. Shared small pool/spa and BBQ grill, in common area. Also shared use of paddle boards, kayaks, and bicycles. You can walk or ride bik.......read more

Studio
Sleeps 2
Apartment

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Summerland Key Cottage - 4.0 Star Review

These cottages are not fancy, but clean and comfortable. Plenty of space for your boat trailer, public ramp just around the corner. We have 2 cottages on this property. This is unit #1. This cottage does not have an ocean view but is on the open water. Just a few steps you can walk out and lounge by the ocean.
To see our other units features an.......read more

Studio
Sleeps 2
Cottage

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Big Pine Key Private vacation home - 5.0 Star Review

Modern 3 bedroom 2 bath stilt home centrally located in Big Pine. Large heated swimming pool with tanning ledge. Corner canal front lot with 120 ft of dockage. 5 min. to the Gulf and 10 min. to the Atlantic. Close to the Winn Dixie grocery store and Big Pine Park with tennis, basketball, skateboarding, racquetball, playground. Free public boat.......read more

4 Bedroom(s)
Sleeps 7
Private vacation home

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Key West Condo

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

BACKCOUNTRY VIEWS is the ideal vacation setting for those looking to relax in a peaceful, tropically inspired condo that offers an incredible view of the water and breathtaking Key West sunsets. Located in the private gated community of .......read more

2 Bedroom(s)
Sleeps 4
Condo

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Big Pine Key Private vacation home

Pine Channel home is located on one of the best deep water canal for great access to the Atlantic and/or back-country. This Lower Keys home has an open great room that includes the kitchen with an island Beautiful lower keys private home, gated with 3 bedrooms 2 baths bonus downstairs game room sleeping 10 comfortably, 2 boat lifts 6000 lb and 15.......read more

3 Bedroom(s)
Sleeps 10
Private vacation home

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Tavernier Private vacation home

Beautifully updated 1 bedroom unit in Tavernier. Open concept. Recess lights and waterproof laminate throughout. Large living room. Good size bedroom. New kitchen with quartz counters and stainless-steel appliances. Updated bathroom with walk in shower. New mini split air conditioning unit. Walk to Harris Park!.......read more

Studio
Sleeps 3
Private vacation home

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Key Largo Apartment

Long Term/Annual Rental, Unfurnished, Water and Electricity Included. 2 Story CBS Single Family House, Built 2021, Located @ mm 102/Ocean Side. 3 Spacious Bedroom, 2 Ample Bathrooms, Laundry Room Hook-Up Ready to Accommodate Washer and Dryer. Open Concept Living Area with Amazing Ample Kitchen. Move-In Requirements: 1st Month + 2 Month Security Dep.......read more

3 Bedroom(s)
Sleeps 6
Apartment

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Key Largo Private vacation home - 5.0 Star Review

Great home with everything you need to enjoy a great vacation with access to a private park with a boat ramp. Close to many great places in the area such as John Pennekamp Coral Reef State Park, many places to eat in great restaurants and enjoy live music, fish, snorkel, kayak and more.
Property has plenty parking space even for a boat. Internet.......read more

Studio
Sleeps 4
Private vacation home

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Islamorada Private vacation home

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

2 Bedroom(s)
Sleeps 8
Private vacation home

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Islamorada Private vacation home

A beautiful home on the bay, in sunny Islamorada, Florida. You have access to one of the only beaches in Islamorada, which is a quarter mile from the house. A quick boat ride and/or key access if you’d like to travel by car. Dock space has over 60 feet with your own personal ramp (ramp only accommodates smaller boats, 3,000 pounds or less). Amazing.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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Marathon Private vacation home - 5.0 Star Review

Reef Retreat, a beautifully appointed Coastal Modern home perfect for your vacation needs.  This 2 bedroom, 2 bath duplex has been meticulously maintained and newly furnished.
1420 sq. ft of living area and very spacious bedrooms and modern baths.
The master bedroom has a beautiful extra large modern and spacious on suite bath.

The kit.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Summerland Key Private vacation home - 5.0 Star Review

Welcome to 'The Blue Pearl' – the ultimate destination for large families or multiple families seeking an expansive and accommodating retreat. With two distinct living areas, this spacious haven offers ample room to gather together or find your own space for relaxation. Step onto the sand and revel in the 125 feet of oceanfront that's all yours. Wa.......read more

4 Bedroom(s)
Sleeps 12
Private vacation home

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Key Largo Private vacation home

Rent a $2 million Mermaid House Best Location Central Key Largo walking distance from restaurant
Rent 3/2 second floor with 1/1 third floor in law quarters separate entrances perfect for a family get away. Boat dock available for two boats.

Charming Waterfront Home suitable for multiple families or multiple boats. Rent 3/2 or 4/3 (pm for.......read more

4 Bedroom(s)
Sleeps 9
Private vacation home

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Key West Private vacation home - 5.0 Star Review

Sapphire Sabbatical

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Beautifully situated among the palms and right on a canal that leads out to open water, this three-bedroom home on Big Coppitt Key is the perfect Florida Keys escape for boating e.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Marathon Private vacation home - 5.0 Star Review

Welcome To Your HotTub Hideaway! PRIVATE, SECLUDED, INTIMATE AREA (JACUZZI, PUTT-PUTT, BBQ, CORNHOLE, PRIVATE BAR, POOL TABLE & MORE) FRESHLY REMODELED & CLOSE TO ALL THE BEAUTIFUL WONDERS MARATHON, FL (THE HEART OF THE FLORIDA KEYS) HAS TO OFFER. BRING THE TOYS - PARKING FOR ALL YOUR FL KEYS NEEDS! OVERHEAD LIGHTING TO SPARK UP THE NIGHT & ALONG W.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Key West Apartment

Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the newly built property.

PLEASE NOTE:
- The resort fee is not included in the d.......read more

Studio
Sleeps 4
Apartment

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Islamorada Private vacation home

Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-park.......read more

Studio
Sleeps 4
Private vacation home

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Key Largo Private vacation home

Beautiful house with water view in Key Largo, located within walking distance of markets, parks and restaurants to make your stay in the Florida Keys a unique experience.
Large living room with open kitchen fully equipped with new appliances, impeccably furnished, 3 bedrooms and 3 full bathrooms. Large master bedroom with 2 double beds, TV and J.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Key Largo Private vacation home - 5.0 Star Review

The spacious yard has room for everyone to spread out in comfort and enjoy a vacation at their own speed.
Beat the heat with a cooling soak in the pool, or take one of the kayaks out to explore the neighborhood's canals.
Enjoy happy hour beverages under the shade of the 2 palapa huts. Fire up the grill in the fully-equipped outdoor kitchen .......read more

3 Bedroom(s)
Sleeps 10
Private vacation home

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