If you’re planning a getaway to Southwest Florida and don’t want to leave your furry friend behind, you’re in luck! Destination Paradise offers a variety of SW Florida pet-friendly vacation rentals that allow you to enjoy a serene and enriching holiday without parting ways with your beloved pets.
From cozy cottages to luxurious beachfront homes, the region offers something for everyone. Here are 10 magnificent pet-friendly vacation rentals, each with unique features and charm.

The President – 206
In the heart of Lido Key, The President – 206 is a beautiful three-bedroom, three-bathroom home. Ideal for families and groups, this rental offers close accessibility to the amenities of Lido Key while maintaining the ambiance of a secluded oasis. Walk just 150 yards to enjoy the vibrant nightlife at St. Armands before coming back to unwind by the heated pool and spa. The beautiful gated home is surrounded by colorful landscaping and a stucco privacy wall. Included with two bicycles for touring the island, this pet-friendly rental ensures a peaceful and memorable stay around amidst tropical palms.
The Beach Bungalow Siesta Key – 205
The Beach Bungalow Siesta Key – 205 is a superbly renovated four-bedroom, three-bathroom beach house that combines old Florida charm with contemporary luxuries. With its screen-covered lanai and an outdoor lounge area complete with a grill and shower, relaxation is guaranteed. Our professional cleaning service follows enhanced protocols to ensure the utmost hygiene with a six-hour in-depth cleaning session and a 24-point property inspection. You can vacation worry-free and enjoy amenities like the ping pong table or balcony. This pet-friendly rental is conveniently located near the beach, downtown Siesta Key, and multiple golf courses.


Seaside Sunrise – 3141
Located directly on the beach, Seaside Sunrise – 3141 is a five-bedroom, four full bathrooms & two half baths marvel offering unrivaled ocean views. This multi-level home is designed for comfort, catering especially to families with older people and children. Situated on the beach side of A1A, only four miles north of St. Augustine’s north bridge, Seaside Sunrise is the epitome of beachfront vacation rentals in Anna Maria Island. Enjoy the adventure of shell hunting, surfing, fishing, and swimming, all just steps away from your backyard.
Jetties Pointe Cottage #1
Jetties Pointe Cottage #1 is a delightful two-bedroom, one-bathroom property located on the scenic Casey Key. This vacation cottage offers panoramic Gulf views and spacious interiors equipped with comfortable amenities to enhance your stay. The screened-in back porch provides a perfect vantage point for the mesmerizing Gulf Coast sunsets. With tikihuts, firepits, and grills onsite, this property encapsulates the essence of paradise. If you’re browsing through our Casey Key vacation rentals, this is the perfect place to create unforgettable memories with your family and fur babies!


Sea Spray – 3001
Sea Spray – 3001 is a luxurious, dog-friendly rental located directly on the Atlantic Ocean. This spacious home features four bedrooms and three bathrooms, offering breathtaking panoramic views of St. Augustine Beach. Imagine waking up to spectacular sunrises and enjoying moonrises over miles of pristine beach. This St. Augustine beach vacation rental offers endless activities, from beach walks and fishing to surfing and shell searching. Explore the historic town of St. Augustine and enjoy all the amenities at the Serenata Beach Club, including pools and a fitness center.
Tropical Haven *A
Located just three miles from Anna Maria Island’s beaches, Tropical Haven *A is a remodeled two-bedroom, two-bathroom property perfect for a small family with pets. The backyard resembles a resort, complete with a large heated pool and a Baja sun shelf. The open-concept home features a fully equipped kitchen and a private deck for outdoor dining. You’ll also be very close to local attractions such as golf courses, fishing spots, and entertainment venues. If you’re looking for Anna Maria Island beachfront vacation rentals, this property puts you right in the heart of the action.


The Lookout – 891
Spanning an expansive 6,300 square feet, The Lookout – 891 offers five bedrooms, six full bathrooms, and one half-bath. This Siesta Key gem provides a gorgeous waterfront experience with private terraces on the third and fourth levels that offer stunning sunset views. Why not indulge in this luxurious retreat’s amenities, including a private pool, hot tub, and multiple outdoor living spaces? The presence of cozy patios, fire pits, and fireplaces makes this an ideal pet-friendly vacation rental for large families. A street-legal golf cart adds the final touch of convenience.
Lido Sands – 213
Located on the shore of Lido Key, Lido Sands – 213 is a luxurious 4-bedroom, 3-bathroom home just steps away from Florida’s famous waters and beaches. This spacious property has a stunning patio area where everyone can soak in the Florida sun or unwind in the heated pool and hot tub. The outdoor amenities include a fenced-in pool, an outdoor grill, four bicycles, beach toys, chairs, an umbrella, and a cart. Furthermore, the home is within easy walking distance to Lido Beach and St. Armands Circle, known for its vibrant shopping and dining options. This property stands out among other Lido Key vacation rentals.


Rustic Sands – 650
Imagine waking up to breathtaking island views in this Siesta Key vacation rental. Rustic Sands – 650 offers three bedrooms and three bathrooms on a peaceful street. The private pool area is perfect for enjoying Florida’s mesmerizing sunsets, while the grill area provides a delightful space for hosting family cookouts. This enchanting Siesta Key rental comes with a refreshing pool, a luxurious hot tub, and a nook area with a wine and coffee bar. The smart TV in the living room ensures endless entertainment streaming options. Located on the north end of Siesta Key, this rental offers strategic access to The Village, Siesta Beach, Southside Village, Selby Gardens, and downtown.
High Tide – 170
For those looking for a more secluded experience, High Tide – 170 might just be the ideal choice. This 5-bedroom, 4-bathroom pet-friendly home is less than 500 yards from Shell Beach and only a 5-minute drive to Siesta Key Beach. The large private pool patio, surrounded by lush tropical palm landscapes, provides ample space for everyone to relax. The home features a heated pool, spa, a propane fire pit for memorable evenings, and a grill for cooking up delicious meals.

Plan Your Visit
Discover the perfect Southwest Florida vacation rental with Destination Paradise. Explore our selection of properties and book your dream getaway today!
Book Your Pet Friendly SW Florida Vacation Rental With Destination Paradise
With so many beautiful and accommodating vacation rentals in Southwest Florida, it may be challenging to choose just one. However, rest assured that each of these properties offers a unique and memorable experience for both you and your pet. Whether you’re drawn to the historic allure of St. Augustine Beach vacation rentals, the pristine coastline of Anna Maria Island, or the luxury of Lido Key vacation rentals, Southwest Florida has the perfect pet-friendly rental for your next vacation. These vacation rentals stand out for their exceptional amenities, prime locations, and pet-friendly policies. By considering our pet-friendly vacation rentals at Destination Paradise, you are ensuring a memorable and stress-free getaway for you and your four-legged companion in one of Florida’s most beautiful regions. So pack your bags, grab your furry friend, and head to Southwest Florida for an unforgettable vacation!

