
Cottage holiday rentals in Pine Island
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Pine Island
Guests agree: These cottages are highly rated for location, cleanliness and more.

Walk to Downtown and Waterfront - Private Yard
Steps to Main Street and minutes to beaches, yet tucked away on a quaint prime downtown street. Private yard with grill in terrific location. Walk to restaurants, breweries, shops, and live music. Walk to Dunedin's gorgeous sunsets or drive minutes to award-winning beaches such as Honeymoon & Caladesi Island & Clearwater Beach. Sleeps 6. Two king bed suites and a luxury leather couch that sleeps 2 more. Loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today!
FamilyValueIndoor spaces

Ozello Keys Cottage on Crystal Bay
2/1 Ozello coastal cottage on stilts surrounded by nature, tranquility, and endless views of the water and estuary. Nature lovers paradise. World renowned fishing and scalloping. Regular dolphin and manatee sightings. Relax with the whole family on the large screened back porch providing gorgeous views of the Nature Coast and stunning sunrises over the salt marsh. The open floor plan opens up to a large screened porch with a dining and lounging space with private and expansive water views.
LocationValueHospitality

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.
LocationFamilyGetting around

The Hideaway - Quaint and Peaceful Cottage
1.5 miles from Weeki Wachee State Park. Charming, quiet, quaint cottage, beach theme, quiet neighborhood. 2 bedrooms, 1 bathroom. Utilities, flat screen TV, cable, Netflix, wireless internet, DVD player, DVDs, towels and linens. Fully equipped kitchen with pots, pans, utensils, plates, glasses, coffee cups, wine glasses, coffee maker, air fryer, toaster and blender. Outdoor sitting area with a charcoal grill and a fire pit. Bring boat or kayaks. Park your boat on the property.
ValueFamilyKitchen

Screened Lanai /Clear Kayak / Waterfront / Fire Pi
Funky Flamingo River Cottage is a hidden gem on the Weeki Wachee River, designed for fun, relaxation, and adventure. Enjoy a no-see-um screened lanai, a comfy king bed, Smart TVs in every room, and a fully stocked kitchen. Paddle with manatees in our clear kayak, float on the lily pad mat, or unwind by the fire pit. With games inside and out, a hammock, and direct water access, it's the perfect escape—just off the main river, between the State Park and Roger’s Park.
FamilyLocationLaundry

Serendipity Lake private dock, canoes & kayaks
Please note the 15.5% Host Service Fee is an Airbnb fee, they chose the name, host do not collect this fee. FL is in a drought, water levels are 8ft + lower than normal. You can still enjoy fishing and kayaking on our direct waterway. We do provide kayaks and canoes to enjoy the lakes. Plenty of room for outdoor games and activities. Pet friendly. Just a short drive to downtown Inverness and 30 minutes to Crystal River, Dunnellon or Homosassa. Simply perfect!
FamilyLocationIndoor spaces

Private Country House | 16 Guests | Gatherings
Bring the whole family to this private 5-acre retreat, situated in one of the few hilly regions of Florida. Enjoy privacy, nature, spectacular sunsets, and starry nights—perfect for relaxing or enjoying outdoor activities. ⚠️ Gatherings require prior approval—please contact us before booking. Note: There is another house on the property that may be rented by other guests. Both are completely private, with no shared areas or parking.
ValueLocationAccess

Ozello Waterfront Cabaña - minutes from the Gulf!
Calling all outdoor adventurers—this cozy waterfront cabin is your perfect basecamp. Launch straight from your private boat slip, then return to clean your catch at your own fish/scallop station. Grill up dinner on the back deck while soaking in epic water views. Whether you're fishing, scalloping, kayaking, or exploring Florida’s wild coast, this spot puts you in the heart of it all—rustic comfort meets real adventure.
ValueLocationBathroom

PARADISE POINT on Weeki Wachee (Boat Welcome)
Find tranquility at Paradise Point, a charming, private STUDIO home so there is not a separate bedroom. Our canal feeds into the Weeki Wachee River just before Rodgers Park. Short, easy paddle, (less than a quarter mile) to the amazingly clear, turquoise rivers. Stunning views from the back porch. Don't miss breathtaking sunsets on the water and watch for manatees, dolphins, and otters. ⭐️ PLEASE NOTE: 🐾 NO pets!
LocationValueCleanliness

Whispers of Country Where your soul will Wander.
The Shebeen – a charming retreat nestled along the Brooksville ridge, on a picturesque working dairy farm. Here, adventure meets relaxation in a space designed for, reflection, and a bit of romance. Let the rhythmic sound of the farm surround you as you step into a world where time slows, and every moment feels like a sweet escape. Book your stay now and find a little magic in every moment.
LocationFamilyParking

A Dream Cottage!!!
This property has 200 feet of river frontage. It is located next to Rogers Park & beach on the Weeki Wachee river. The living facility is a renovated trailer and large vestibule with a bar and screened patio area. There are a charcoal grill, kayaks, cable TV and Wifi available for entertainment. The location is peaceful for your enjoyment!
LocationValueQuiet

The Aripeka Shack
The "Shack" is our rustic weekend getaway in Aripeka, one of a few remaining "Old Florida" fishing towns. A great place to enjoy Florida nature as it used to be. Located between Hernando Beach, Spring Hill, and Hudson; Aripeka is an easy drive to the many attractions in the "Nature Coast" and the Tampa/Clearwater/St. Pete area.
LocationFamilySleep quality
Popular amenities for Pine Island cottage rentals
Cottage rentals with a hot tub

Lush Harbor Oasis with Private Hot Tub
ValueLocationHot tub

Pink Gulfside Cottage, Steps to Beach, Pets OK
LocationFamilyWalkability

Shelter from the Storm | Weeki Riverfront Escape
FamilyLocationDecor

Beachy Keen Cottage A only steps to the Beach
LocationFamilyAmenities

Cozy Lake Cottage w/ Hot Tub + Boat Parking
FamilyValueHot tub

Gorgeous farmhouse with pool in Tampa Florida
LocationValueQuiet

Breezy Botanical Bungalow
ValueFamilyBathroom

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail
ValueLocationGetting around
Pet-friendly cottage rentals

Cozy Cottage! “ Steps away from Kings Bay!”
FamilyValueQuiet

Luxury Beach Cottage | Walk to Dining & Sunset
ValueLocationParking

Anneliese's Cottage
FamilyValueAccuracy

Beautiful Beachfront Cottage on the Water
FamilyValueCheckout

1950's Cottage in Crystal River
ValueFamilyComfort

Cocos Cottage Summer fun! 10% off 6/1-8/31, 2026
FamilyLocationAir conditioning

Coral Sands II ~Seaside Coastal Modern 2/2
FamilyLocationCheckout

Charming Blue Bungalow With Amazing Yard
FamilyLocationComfort
Private cottage rentals

Cozy Renovated Cottage, Pet-Free Retreat
LocationFamilyAccess

Trendy Seminole Heights Flamingo's
LocationValueCheckout

BeachBunkies Cottage 2. Four miles to the beach!
ValueFamilyBiking

1BR House
FamilyLocationView

Ground-floor, direct beachfront 1BR | on the Gulf
FamilyLocationSolo travel

Roe Family Lake House (Lake Mcleod)
ValueFamilyBathroom

Kayak Kottage: waterfront, kayaks, bikes, dockage
LocationValueAccess

Louisa's Cottage
FamilyLocationAir conditioning
Destinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Panama City Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Destin Holiday rentals
- Hollywood Holiday rentals
- Savannah Holiday rentals
- Jacksonville Holiday rentals
- Hilton Head Island Holiday rentals
- Weeki Wachee Springs
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Rainbow Springs State Park
- Amalie Arena
- Dunedin Beach
- Hard Rock Casino
- University of South Florida
- Epperson Lagoon
- Sand Key Beach
- Weeki Wachee Springs State Park
- MidFlorida Credit Union Amphitheatre
- Three Sisters Springs
- Splash Harbour Water Park
- Crystal River Archaeological State Park
- Fort Island Beach
- Adventure Island
- World Equestrian Center
- Honeymoon Island State Park
- Fred Howard Park
- Sunset Beach
- The University of Tampa
- Homosassa Springs Wildlife State Park
- Tampa Convention Center





