
Holiday rentals with a kayak in Homosassa
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Homosassa
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Firepit, Golf Cart, Kayaks, Pedal Boat, Fishing!
Welcome to Azalea by the Sea, your perfect vacation escape! Enjoy endless water activities and relaxation right in your own backyard. Highlights You’ll Love: •🛶 Kayaks for exploring the waterways •🌊 Water Mat for fun on the water •🔥 Fire Pit for cozy evenings under the stars •🎯 Cornhole Boards for friendly competition •.🚗 Golf Cart •🌿 5 Minutes to Weeki Wachee River — perfect for kayaking, paddleboarding, or spotting manatees •🎵 Nearby Bars & Restaurants with live entertainment every night!!

Private waterfront house with large outdoor bar
Enjoy waterfront views while sipping a cocktail at the giant outdoor bar. Two bedrooms offer queen beds in each and a pull-out queen-size sofa bed is in the living room. Close to popular Crumps Landing Restaurant. The Riverside Marina is nearby to launch your boat. There is ample parking for a boat trailer. Canal access to Halls River & Homosassa River for flats boats or pontoon boats only. Must be able to lower bimini to go under Halls River Bridge. Property includes three kayaks and one canoe.

Weeki Wachee Pirate House - 6703 W. Richard Dr.
Embellish in this once in a lifetime, perfect getaway on Weeki Wachee River. A local favorite! Fully furnished pirate themed, 500 sq ft home with 1 bedroom 1 bath full kitchen and sofa bed. It has everything needed to create unique memories. Swim with manatees in the crystal clear spring-fed river. Have your coffee on the porch over looking the water and your favorite drink around the fire at night. Kayaks are included. Minutes from Weeki Wachee mermaids, Pine Island Beach and Homosassa Springs.

Undebatable
This one bedroom house offers one queen bed and a pull-out sofa to sleep a total of 4 people. The house offers a private boat ramp, docks, and quick access to the gulf. Includes Wifi, 2TVs, washer/drier, fire pit, grill, coffee maker. Enjoy sunsets, nature walks, and fishing from the docks. Clean, Clean, Clean! EVERYTHING is washed after each guest including sheets, towels, All blankets, bed comforters, and even decorative pillow cases. All handles, knobs, remotes and shower are sanitized.

🏝Waterfront Pool & Dock, Close to Springs & Gulf🎣🌞
Bring friends & family to this fully remodeled and decorated home. It features a screened in pool, multiple fireplaces, and floating dock to tie up your boat(s) in a deep water canal with direct access to the Gulf and 3 Sisters Springs. Enjoy swimming with the manatees, scalloping, fishing in the gulf, kayak (2 inc.) & tube down the river, or shop & eat in Downtown Crystal River. The home has over 2,300 sq ft, 3 bedrooms / 3 baths making it a comfortable getaway for any season and occasion.

Chassahowitzka/Homosassa Waterfront Home
Remodeled Water Front Property with beautiful furnishings. There are two bedrooms, two baths, and a large lanai overlooking the canal. The kitchen is fully stocked with everything you need to prepare meals. Walking distance to Chassahowitzka campgrounds, a bait shop, and a bar/restaurant. Fish off the private boat dock: covered parking, bonus lanai room. We have two fishing kayaks available for use. THE OWNER TAKES NO LIABILITY FOR THE USE OF KAYAKS. Pet must be approved before check-in.

Retro Retreat, Waterfront,Kayaks,Boatslip
💦WATERFRONT HOME ON CANAL IN GREAT LOCATION. Use our KAYAKS to visit the MANATEES at 3 SISTERS and all the local springs. 🔴 BOAT SLIP for SCALLOPING! 🔴 POLES to fish right in the backyard. 🔴 1 man, 1 woman bicycles, fire pit table and grill. 🔵 UNIQUE RETRO RETREAT Vintage style fridge in fun, open concept kitchen, record player/records and comfy couch. We are close to everything... SWIMMING WITH MANATEES!! KAYAKING IN THE SPRING FISHING SCENIC/AIRBOATING SCALLOPING

Stilted 2BR canal home, full kitchen, yard, pets!
This unique place has a style all its own. Nestled upon an actual island within the Ozello Keys, Crystal River! Backwater canals to the Gulf of Mexico is the view from this loft style, stilt home. Recently renovated with all the conveniences guests love into the overall design. The property offers plenty of parking for all your toys (RV's require prior Host approval). Easily fits up to 8 vehicles. Dog friendly! FOUR Kayaks/Paddles included with your stay! Fully equipped home!

Waterfront Cottage 2BR 1B
This charming house is located on nearly an acre of woodland. Fish from the dock of the screen room on the canal or kayak to the nearby lake. Relax in the private backyard Jacuzzi. Bike on the nearby Withlacoochee Trail. There are 2 bedrooms plus living room sleeper sofa, and a lanai with a day bed. Fully furnished. Orlando theme parks are 1 1/2 hour away, Busch Gardens 1 hour. Close to Weeki Wachee, Homosassa and Crystal River for manatee viewing or scallop season.

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.

The Banyon House 2br 2Ba on Canal + Kayaks
Relax with family and friends at this beautiful property. Enjoy kayaking right from the dock on the property. There is a lovely covered patio where you can enjoy meals cooked in the fully stocked kitchen. There are two bedrooms that are both en-suite. For additional sleeping there is a sleeper sofa in the lounge. We will accommodate Dogs (up to two) but NO CATS... Owner is highly allergic. There is a $75 additional pet fee per stay.

Florida Fishing and Kayaking Paradise
Old Florida remote Fishing utopia in the Ozello Island Keys community of Crystal River, Fl. Amazing views from wrap around deck! 4 kayaks , 1 Canoe w/ fishing/swim gear. Swim off Floating Dock and Cold/Ice Bullfrog Spa! Perfect for 1 to 2 sm. families. Stocked kitchens and grill. TV Cable WIFI. Fenced yard, for kids/dogs. Boat ramp and covered parking. Bottom Floor under renovation winter 2025.
Popular amenities for kayak rentals in Homosassa
House rentals with a kayak

Homosassa home on the water with kayaks.

Homosassa River with Springs & Gulf Access

Homosassa River Fish Camp

Mermaid Cove & Flip Flop Tiki hut

Sassafied!

Seahorse River House @ Weeki Wachee

Relaxing Escape

Waterfront in Old Homossassa w/hot tub and kayaks🎣
Cottage rentals with a kayak

Relax Canalside at our Cottage, fast 200mbps wifi

Cozy Cottage! “ Steps away from Kings Bay!”

PARADISE POINT on Weeki Wachee (Boat Welcome)

The Lakeside River House

Kayak Kottage: waterfront, kayaks, bikes, dockage

The Hernando Lake House

A Dream Cottage!!!

Coastal Cottage Getaway
Cabin rentals with a kayak

Chaz River Charmer

Private Waterfront Cabin Retreat with Kayaking

Stunning Withlacoochee Riverside Cabin 5BR 4BA 16+

A Frame Stream Dream Cedar Cabin-WeekiWachee River

Charming Lakeside Getaway - 1BR with Serene Views

Tin Roof Cabin at The Cove

A-Frame with Rainbow River access via Com. Park

Cotee River Guest Cabin
When is the best time to visit Homosassa?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $303 SGD | $316 SGD | $303 SGD | $289 SGD | $293 SGD | $302 SGD | $379 SGD | $325 SGD | $284 SGD | $264 SGD | $283 SGD | $255 SGD |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Quick stats about holiday rentals with a kayak in Homosassa

Total holiday rentals
Explore 70 holiday rentals in Homosassa

Nightly prices starting at
Homosassa holiday rentals start at $88 SGD per night before taxes and fees

Verified guest reviews
Over 3,500 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
70 of Homosassa holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Homosassa rentals

4.9 Average rating
Homosassa stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a kayak United States
- Weeki Wachee Springs
- Tampa Palms Golf & Country Club
- Rainbow Springs State Park
- Fort Island Beach
- Fred Howard Park
- Hunter's Green Country Club
- Weeki Wachee Springs State Park
- Homosassa Springs Wildlife State Park
- Three Sisters Springs
- World Equestrian Center
- World Woods Golf Club
- Crystal River Archaeological State Park
- Sunset Beach
- Snowcat Ridge
- Tarpon Springs Castle Winery
- Howard Park Beach
- Hunters Spring Park
- Werner-Boyce Salt Springs State Park
- K P Hole Park
- Cedar Lakes Woods & Gardens
- Florida Horse Park
- Sholom Park
- The Canyons Zip Line and Adventure Park
- Crystal River




