
Vacation rentals with a kayak in Holmes Beach
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Top-rated kayak rentals in Holmes Beach
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

3/3 condo with Pool - 2 miles to beach
Our Happy Place is a stylish 3-bedroom, 3-bath condo in the exclusive Margaritaville – One Particular Harbor at Harbour Isles. This spacious retreat features a fully stocked kitchen with island seating, a dining area for six, and a cozy living room that opens to a screened balcony with serene lake and nature views. Each bedroom offers comfort and privacy, with two en suite baths and thoughtful touches like remote-controlled ceiling fans and blinds. Guests can enjoy community amenities including

Heated saltwater pool home - turf putting green
Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

Beautiful Waterfront Home on the Alafia River.
Beautiful Waterfront Single Family home on the Alafia River leading to Tampa Bay and the Gulf of Mexico. Bring your boats, jetskis, Kayaks, water toys, fishing rods, etc. Riverview Civic Center and Boat Ramp is literally a couple of blocks away from the property and trailer parking is available at the property. If it’s your lucky day, you will see manatees, dolphins, snook, redfish and stingrays right from the dock. Excellent fishing, restaurants and nightlife all on the river or by vehicle.

Hibernate in our Bear Creek Home
This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

Waterfront Pool Oasis •Kayak, Games & Sunset Views
Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

Steps to Beach+bikes VaCay getaway on PaG island
Escape to charming Pass-a-Grille BeachHouse—your perfect beach getaway! Steps from Florida’s most beautiful beach, this cozy coastal retreat features hardwood floors, a beach wagon, smart TV's (also in bedroom) w/sports package, a sun patio, 2 bikes to explore. Soak up the old Florida charm and island vibes in this peaceful slice of paradise. This delightful one-bed -bath town-home style rental is situated steps away from the beautiful white sand beach that stretches for 7 miles.

Waterfront Townhome w/ Heated Pool & Balconies
Relaxation awaits you the moment you step in to Bahia Bungalow, a 2 Bedroom, 1.5 Bath town home nestled in Little Harbor Resort. Little Harbor is located on a partially private guest reserved beach in Ruskin, a short drive from Tampa, Sarasota & St. Pete. The resort overlooks Tampa Bay & features a heated outdoor pool, basketball and pickleball courts, fitness area, a playground & a marina. Dining within the Resort include a bay-view restaurant, a poolside bar/grill.

Waterfront Gem/ Pool Spa+ Dock/ Near Bridge Street
Anna Maria Waterfront oasis! **5 min walk to beach, private dock, pool heat included!!** Relax in the private heated pool, sip coffee on the dock, or walk to the beach. This bright, updated home has spacious living areas, a stocked kitchen, smart TVs, fast Wi-Fi, and cozy beds. Great for families or couples! Grill by the pool, dine under the stars, or fish from the dock. Includes washer/dryer, beach gear, and parking. Your peaceful, sunny getaway awaits—book now!

Discounted October Stays w/Private 30' Dock & Pool
* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

Las Palmas Beach Rentals unit 2
Unit 2 Ground floor;800 sq ft; patio; limited beach view . Steps to the white sandy beach across the street Free parking to registered guest. Fully equipped kitchen with markets nearby, Restaurants and shopping, within walking or hop free trolly. Trolly stop nearby. Linens and basic supplies are included. Overnight guest are welcome to arrive early to adventure the island, stay parked until after sunset on departure day.

Island Breeze! Direct to beach access!
Welcome to Island Breeze, your serene getaway just 2 blocks from the beach and nestled in the charming Bradenton Beach. This cozy 2-bedroom, 2-bathroom retreat offers all the comforts of home, including air conditioning, high-speed wireless internet, and a fully equipped kitchen. Sleeps up to 6 with the brand new sleeper sofa. Perfect for small families or a group of friends looking to unwind and enjoy the beach life!

Waterfront condo on top floor @ Boca Ciega Resort
Great view of water. Especially beautiful sunsets! Top floor end unit for privacy. Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking the intercoastal or stay indoors and enjoy puzzles and games.
Popular amenities for Holmes Beach kayak rentals
House rentals with a kayak

Kayak + Canal View | Next to Anna Maria & Reserve

Sea Vue -King Beds | Stunning Views | 2MI to Beach

Waterfront Manatee Home Pool, Dock, Optional Boat

Beautiful Tampa Pool/ Hot Tub Home- Spacious Yard

5 Bed/4 Bath Waterfront Pool Home in Apollo Beach

Piece of paradise in Indian Rocks Beach.

AMI Dock of the Bay - "On the Water" 1st Floor

New Waterfront house pool hot tub golf cart kayaks
Cottage rentals with a kayak

Anna Maria Cottage w/Golf Cart

Lido Key Beach Bungalow with Private Heated Pool!

Little Manatee River Cottage

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

Cottage & Tree ~ by the Sea

2/2 Charming Riverfront Cottage w Deck & Kayaks

Alafia River Cottage

Steps To The Beach, Private & Heated Pool, Renovat
Other vacation rentals with a kayak

Private Dock~Covered Pool~Hot Tub~Game Room Fun!

Resort-Style Ground Floor Suite Heated Pool/Spa

Waterfront Retreat | Heated Pool & Boat Dock

Coastal Farmhouse & Pool

Coastal Haven w/pool in Bradenton

Waterfront Suite-20 min to Gulf Beaches

Cozy Coastal Getaway

Flamingo Flair & Waterfront Air — Pure Paradise!
Quick stats about vacation rentals with a kayak in Holmes Beach

Total vacation rentals
Explore 30 vacation rentals in Holmes Beach

Nightly prices starting at
Holmes Beach vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

Verified guest reviews
Over 620 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Holmes Beach vacation rentals include wi-fi access

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

4.9 Average rating
Holmes Beach stays are highly rated by guests—averaging 4.9 out of 5!
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- John's Pass
- Raymond James Stadium
- Dunedin Beach
- Busch Gardens Tampa Bay
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Cortez Beach
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- Adventure Island
- River Strand Golf and Country Club
- Tampa Palms Golf & Country Club