Cottage holiday rentals in Safety Harbor

Walk to beach shops food drinks “The Sweet”

Cozy, romantic, 1 king bed, super cute and super sweet! Just a short walk to beautiful Indian Rocks Beach, nature parks with trails, shopping, orange grove, and many restaurants and fun beach bars! Guests have private entrance, private full bath, kitchenette, sofa sleeper, large back yard with fire pit, bbq grill, beach chairs, wagon and cooler. Zoning permits 2 people per bed only and one on futon. All guests must be listed on the reservation. No Pets allowed. Florida State License # DWE6215889

Cooper Cabin: Cute, Adorable, Standalone Studio

Cooper Cabin is a super cute and sparkling clean stand alone studio with a full eat-in kitchen and bath. Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue! Located within walking distance of all things Tarpon Springs and just a short 7 min drive to Fred Howard Beach, Cooper Cabin is decorated with fun decor and a relaxing front porch balcony with bistro set. Bikes and beach gear provided!

Charming Downtown Cottage – Walk to Everything!

Stay in this charming 1920's cottage, where everything is just a stroll away. Walk to the local restaurants, breweries, and shops on Main St, or take a leisurely walk to the marina for sunsets. With its prime location, it is perfect for exploring the heart of Dunedin on foot. Let’s walk and discover all that this vibrant area has! Your beautifully appointed cottage is a great retreat after beach fun, baseball or biking, and is an easy stroll home after an evening enjoying the local music scene.

Clearwater Cottage Short Drive to Beach & Dunedin!

Perfectly nestled between the quaint town of Dunedin & Clearwater. Just a short drive across the bridge & you’ll be Sinking your toes into the beautiful white sandy beaches of Honeymoon Island State Park or Clearwater Beach. Enjoy Honeymoon Island natural beauty or exciting tourist attractions of Clearwater beach! Take a cruise on the dinner boats to watch the beautiful sunset. Walk or rent a bike & explore the Pinellas trail. Kayak or jet ski the Gulf. Max 5 Adult guests with government ID.

Artsy guest house; near downtown w/ private patio

This uniquely decorated guest house is a private oasis with a lovely, private patio. The house is decorated with Latin American art from the owner's collection & travels. Only 11 blocks to downtown and very close to grocery stores, art galleries and all the night light life St. Pete offers. The home has a full kitchen and a very comfortable bedroom for one or two people. A perfect location for those that want to experience a comfortable and relaxing place. Only 12 block walk to Tropicana.

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Cool Breeze Cottage by the Bay in South Tampa

Great location for this cottage one block from Infamous Bayshore Blvd. Smart Tv's and quiet back porch with fire pit makes this location perfect for vacationers. Short walk to Bayshore blvd with scenic views of downtown Tampa and beautiful Tampa Bay water ways. Come and enjoy biking, running, skating or just walking along this 4 miles continuous waterfront walkway. You will have views of Tampa Bay on one side and views of multi-million dollar homes on the other during your stroll.

Adorable Villa 1 min to Downtown Dunedin

Welcome to our 1/1 cottage-style villa, which is minutes from Downtown Dunedin. Only a short walk to Main Street and a 12 min drive to Honeymoon/Caladesi Island! Walk to the Pinellas Trail, breweries, eateries, waterfront marina, and Blue Jay baseball stadium. Enjoy award-winning cuisine, live entertainment, and breathtaking sunsets before returning to the peace and quiet of your own private area. Dunedin is a gulf cart friend city with local rental available to cruise around town.

Adorable Cottage, Pet friendly, near beach & DT

The Cottage is a beautiful, comfy, clean, peaceful home where you will feel just at home, in the hearth of St Pete. It is in a great location, safe & quiet neighborhood, easy-to-access, just a short drive or bike ride away (5-10 minutes) to many good restaurants, grocery stores, museums, library, coffee place, breweries, hospitals, bars and night clubs in downtown & sandy white beaches. Jumped in the sun runner or public transport to downtown or beaches. Perfect for long stay.

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street, yet tucked away ! Private yard with grill in a prime location. Short walk to Dunedin's waterfront and minutes to beaches. Stroll to Dunedin's restaurants, breweries, shops, and live music. Walk to gorgeous sunsets or drive minutes to award-winning beaches such as Honeymoon Island and Clearwater Beach. Sleeps 6. Enjoy designer décor and two king suites. Loaded with beach & kids’ gear for easy escape. Treat yourself and book this Dunedin favorite today.

Heart of Safety Harbor | Hot Tub | Luxe Comfort

***New upscale mattress installed 4/28/25. This updated designer cottage is one block north of Main Street! The cottage is outfitted with upscale furniture and a private hot tub! It's well laid out with a very open and light living space. It has strong Wi-Fi/cable and also Smart TV in master. It comes with a fully equipped kitchen including a dishwasher and inside full-size washer & dryer.