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13 Best Vacation Rentals in Dunedin, Florida

Travelers love spending time in Dunedin, Florida because of the excellent dining, art experiences, lovely beaches, and Southern charm. When you want to be close to the white sands and emerald waters, it’s fun to book a vacation rental property that feels like home in a tropical paradise. For your next trip to this underrated Florida town, consider booking one of these vacation rentals in Dunedin through Airbnb or Vrbo.

Tropical Paradise Rental Unit Awesome access to a pool and outside lounge area
Credit: Awesome access to a pool and outside lounge area by Airbnb.com

Tropical Paradise Rental Unit

A truly tropical vacation can be all yours when you book a stay at this rental unit in one of Florida’s best beach towns. This highly-rated Airbnb accommodates four guests and has two bedrooms and one bathroom. The rental is on an acre of land in the heart of Dunedin and offers full access to a pool and an outside dining area with a grill. Meanwhile, the beautifully decorated interior has a queen-size bed in each bedroom and a large kitchen with plenty of room to cook. Book this Airbnb to feel like you’re in your own private oasis with everything downtown within walking distance.

Cozy Cottage Dunedin: Two-Bedroom Pool Oasis near Town A pool oasis in a historic neighborhood
Credit: A pool oasis in a historic neighborhood by Airbnb.com

Cozy Cottage Dunedin: Two-Bedroom Pool Oasis near Town

You’ll feel comfy and cozy when you book a stay at this popular Airbnb in Dunedin. It is a two-bedroom, one-bathroom guest house with a private pool in a historic neighborhood. The cottage is close to the Pinellas Trail, Dunedin Marina, Blue Jays Stadium, and some of the best beaches in the greater Tampa area. It has Wi-Fi, a great kitchen, and beach towels and chairs provided. The home is all on one level, with just a few steps to get in and out. The Airbnb host provides guests with coffee and tea supplies, plus some snacks and condiments for cooking. The pool, yard, and brick patio are shared areas with the hosts that live in the main house on the property.  

Captain's Quarters - Capt. Nemo Unit with Free Boat Slow down your pace of life with a stay here
Credit: Slow down your pace of life with a stay here by Vrbo.com

Captain's Quarters - Capt. Nemo Unit with Free Boat

You can rent this waterfront condo on Ward Island in Dunedin for less traffic and a slower pace of life. It is a 900-square-foot condo with two bedrooms and one bathroom for your trip. There are actually three other Vrbo vacation rental units on this property, named Captain Morgan, Captain Kirk, and Captain America. With this particular rental, you’ll have an onsite washer and dryer, a full kitchen, Wi-Fi, and a TV with cable and HBO. There are also lots of shared amenities that you can enjoy while staying at Captain’s Quarters, including two bikes, a dock, a deck/balcony, fishing rods, and BBQ grills.

Grove Keeper Cottage Upper Unit with a Treehouse Atmosphere Lush and tropical landscaping for a true vacation
Credit: Lush and tropical landscaping for a true vacation by Vrbo.com

Grove Keeper Cottage Upper Unit with a Treehouse Atmosphere

Perfect for two guests, this cottage is cozy and feels like being in a treehouse. It is a Dunedin Vrbo rental that is great for a truly off-the-beaten-path Florida getaway when you want to be in a private and comfortable environment. The kitchen is stocked with all the essentials, the furnishings are bright and cozy, and the balcony off the bedroom offers a view of the pool and pond. There is a king-size bed in the bedroom. The property around the home has lots of tropical landscaping to make you feel like you’re on a real getaway. It’s a hidden gem not too far from downtown Dunedin and the hiking and birdwatching nearby at Hammock Park.

Cozy One-Bedroom Tiny Home with Pool Charming and perfect for couples
Credit: Charming and perfect for couples by Airbnb.com

Cozy One-Bedroom Tiny Home with Pool

It’s fun to live the tiny home lifestyle during your trip to Dunedin, so consider booking this tiny house Airbnb with pool access. Two people can comfortably stay, as there is a queen-size bed on the second floor, a bathroom on the first floor, and a kitchen. There is a pool that you can use during your stay that is shared between the four tiny homes on the property. The pool is not heated. It’s just a short drive from the house to the beaches and within walking distance of Dunedin’s restaurants, breweries, and shops.

Tiki Hut Cottage Cute and festive with plenty of privacy
Credit: Cute and festive with plenty of privacy by Airbnb.com

Tiki Hut Cottage

When you’re looking for a fun and unique place to stay in Dunedin, book this Tiki Hut Cottage with two bedrooms and 1.5 bathrooms. Five people can stay here and enjoy the eclectic vibes during a vacation. Guests can use the kitchen, spacious living area, and laundry machines during their stay. It is a pet-friendly Airbnb that allows dogs up to 35 pounds. The property is decorated with lush tropical plants, and there is a pool area with outside seating.

Park Model RV, Sleeps 4 A cozy trailer as your home base for adventures
Credit: A cozy trailer as your home base for adventures by Airbnb.com

Park Model RV, Sleeps 4

This Airbnb rental in Dunedin is a permanently parked RV that is an open and relaxing space. The rental unit accommodates four people and has a kitchen, bathroom, queen-size bed, and double futon. The unit is within two miles of Honeymoon Island State Park and Caladesi Island. Outside the trailer, there is a seasonal pool in the park and activities offered by the resort. You’ll also find a full bathhouse with showers and laundry machines at the resort.

Downtown Dunedin Condo in the Walking District A lovely condo that gets great guest reviews
Credit: A lovely condo that gets great guest reviews by Vrbo.com

Downtown Dunedin Condo in the Walking District

For your trip to one of the best vacation spots in the Tampa area, you can book this condo for four people through Vrbo. It is a two-bedroom, two-bathroom condo with a gourmet kitchen located on the second floor of a mixed-use commercial building. There are two retail shops downstairs. When you stay, you can walk throughout the quaint community and also visit the Pinellas Trail, the island’s beaches, and locally owned businesses. Access to the space is via a secure residential entrance with an elevator.

Coastal Downtown Dunedin House with Bikes Newly renovated and with coastal style
Credit: Newly renovated and with coastal style by Vrbo.com

Coastal Downtown Dunedin House with Bikes

In a space of about 800 square feet, this Vrbo rental house is less than a mile from downtown Dunedin and four blocks from the Pinellas bike trail, one of the top bike trails in Florida. The Vrbo host provides you with four bikes to use during your stay. The rental unit is a coastal-decorated home that has been newly renovated and has laundry machines and a stocked kitchen. The sleeping areas include a king-size bed in one bedroom and a queen-size bed in the other bedroom. If you are traveling with a small child, let the host know, and a travel crib can be provided.

Endless Summer Cottage 2 Perfect for enjoying biking and the beach
Credit: Perfect for enjoying biking and the beach by Airbnb.com

Endless Summer Cottage 2

You can rent this Dunedin cottage for your Florida trip. With enough room for four people, the cottage has two bedrooms and two bathrooms in a location that is ideal for groups that love the outdoors and the beach. From here, Honeymoon and Caladesi Islands are just a 10-minute drive, both of which are beautiful Florida state parks to visit. The cottage has a kitchen with everything you could need for cooking, and there are TVs in the living room and bedrooms. It is part of the Dunedin RV Resort, which means you have access to an outdoor pool, pickleball courts, shuffleboard courts, horseshoe pits, a gym, a dog park, a playground, and various park activities. The Airbnb host also provides you with bikes and beach gear.

The Coastal Retreat Light, airy, and eclectic
Credit: Light, airy, and eclectic by Airbnb.com

The Coastal Retreat

This coastal retreat is a rental unit for up to three guests in Dunedin. It is a studio space with a full kitchen, bathroom, queen-size bed, and twin air mattress for a child. The home is cozy and in a walkable neighborhood. You can bring your dog along as long as you keep the pup on a leash and pick up the waste. There’s a nice outdoor space here, and bikes are available to use. During your stay, you’ll be just three blocks from St. Joseph’s Sound, while three of the area’s hidden gem beaches are just minutes away.

Quaint House in Downtown Dunedin New furnishings and a cozy vibe
Credit: New furnishings and a cozy vibe by Airbnb.com

Quaint House in Downtown Dunedin

To stay in a quaint house during your trip to Dunedin, check the availability of this Airbnb listing. The home sleeps six people and has two bedrooms and one bathroom. All the furniture in the house is new, and the bathroom has been remodeled. It comes with a 60-inch TV, queen-size beds in each bedroom, a sleeper sofa for additional guests, a desk, an elliptical machine, and a full kitchen. Guests enjoy the prime location of this house because it is conveniently located near downtown Dunedin, making it easy to find fun ways to spend your days in Dunedin.

BeachBunkies Cottage 2 Wonderfully located between downtown and the coast
Credit: Wonderfully located between downtown and the coast by Airbnb.com

BeachBunkies Cottage 2

Located four miles from the beach, this Dunedin cottage is a studio space with a bathroom. It can sleep up to four people across its queen-size bed and sofa bed. This is one of two cottages available to rent on the property through Airbnb. Between the two cottages, there are some shared amenities, including laundry machines, a fire pit, lounge chairs, a dining table and chairs, and a grill. The driving ranges, golf courses, and beaches are just a short drive away. Also, the Toronto Blue Jays facility is less than a five-minute walk from the home.  

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