
Vacation rentals with a kayak in Holmes Beach
Find and book unique kayak rentals on Airbnb
Quick stats about vacation rentals with a kayak in Holmes Beach

Total vacation rentals
Explore 50 vacation rentals in Holmes Beach

Nightly prices starting at
Holmes Beach vacation rentals start at ﺩ.ﺇ 441 per night before taxes and fees

Verified guest reviews
Over 1,000 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

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

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

4.8 Average rating
Holmes Beach stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated kayak rentals in Holmes Beach
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

Private Island Old FL Waterfront Heaven on Earth
Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool
Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

Gulf Beach Getaway-STEPS FROM BEACH
This updated condo sits just 54 steps from the white sand of Holmes Beach. Experience dolphin sightings or sunsets from the rooftop balcony. Our renovated kitchen is fully stocked with all the amenities of home. Enjoy plenty of space with a large kitchen and living room and two private lanais. You’ll love this condo’s central location to all Anna Maria has to offer! *License CND5105468 *7 Night minimum stay *6 Occupants max *2 onsite parking spots *Noise curfew is from 10:00 p.m. to 7:00 a.m.

Casa Coquina AMI- Newly Renovated, steps to beach!
Newly renovated single family home , STEPS to the beach ( Direct beach access at the end of the street- 5 houses up from the beach) , private fenced in backyard with heated pool, hot tub & outdoor shower! Steps away from restaurants, bars and shops! 3 bedrooms and 2.5 baths Downstairs complete with a game room including a tv and ping pong table! *if you want to check in/out on any day other than a saturday please message me directly and i will see if the dates you request are available

Waterfront Home Private pool, elevator and dock
Luxury waterfront retreat w/pool, spa, boat ramp & dock! Elevator makes it perfect for multi‑generational family getaways. This brand-new home features airy open-concept living and 4 bedrooms (3 primary en-suites with King). Swim in the sparkling pool, soak in the spa, grill on the BBQ, and dine under the covered patio. Just minutes to Gulf beaches and local dining. Bring your boat and enjoy waterfront living from your own backyard oasis, where you can relax and watch manatees in the canal.

Canalfront Cottage Near the Beach!
Stars on the Water by AMI Locals Duplex in Holmes Beach, Florida VRC21-000115 Perfect for beach and bay lovers alike, Stars on the Water is a charming canal-front vacation home with a private dock, just a leisurely six-minute walk from Manatee Beach! This intimate two-bedroom, one-bath retreat offers stunning water views, a fully equipped kitchen, and a spacious outdoor patio with plenty of loungers and a BBQ grill, ideal for relaxing days in paradise. Located within walking, biking, or

New! Private + 2 min walk to Sand+ Heated Pool!
🏝️Welcome to AMI Beachside Bungalow, a newly remodeled island getaway just a 2-minute walk from the soft white sands of one of the most private and picturesque stretches on Anna Maria Island. This street does not allow public parking for beach access, offering rare privacy and tranquility. ☀️Glowing with natural sunlight and designed for comfort, AMI Beachside Bungalow offers the perfect blend of coastal style and laid-back island living for multi-generational families. VRC# 21-000132

1/2 Block from Beach- Private Boat Dock & 30' Pool
o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

Margaritaville Resort 3BR | Pool | Anna Maria
Welcome to Our Happy Place, a stylish 3BR/3BA condo in Margaritaville at One Particular Harbour, Harbour Isles. Enjoy two en suite baths, a fully stocked island kitchen, dining for six, and a screened lanai overlooking peaceful lake and preserve views. Designed by an interior decorator for a calm, coastal feel. Resort pool, splash pad, and grills on site; Holmes Beach is just 2 miles away. Dog-friendly, with a dedicated workspace for remote days. Sleeps 6 in real beds, no bunks.

Bay Breeze Cottages #3
Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

Pergola Oasis | Walk to Beach + Outdoor Living
Welcome to Salty Palm, a newly remodeled coastal retreat in the heart of Holmes Beach. Just a short walk to the white sandy beaches of Anna Maria Island, this home features a private covered pergola with outdoor lounge seating and dining, creating the perfect space to relax day or night. Steps from shops and eateries, with nearby bike and golf cart rentals, plus access to community amenities including a boat ramp, kayak launch, fishing dock, and tennis & pickleball courts.

Beach Escape | Heated Pool | Walk to Beach & Golf
Escape to Beach Escape, a charming 3-bedroom, 3-bathroom Mediterranean-style house in the heart of Holmes Beach, Florida. Enjoy easy access to the pristine beach, walkable dining and shopping, and a free trolley stop. This home offers a private outdoor oasis with a heated pool, outdoor dining, and a gas grill. Explore the island with a complimentary golf cart and bikes. Experience the perfect blend of relaxation and adventure in this guest-friendly location.
Popular amenities for Holmes Beach kayak rentals
House rentals with a kayak

Manatee Cove: Waterfront Oasis w/GameRoom &HotTub

Historic Wares Creek 3 bedroom with dock access

Waterfront Pool Oasis Kayaks, Games & Beach Vibe

Villa La Concha~West of Gulf Steps to the Beach!

Coastal 2BR/2BA w/ Heated Pool +200 Steps to Beach

Heavenly Hideaway, 3 bdrm, 5 minute walk to beach

“Topside” luxury home in Cortez Village

Destination Relaxation
Cottage rentals with a kayak

Siesta Key Cozy Cottage across from the beach!

Sunny PaG Island rental w/bikes-just steps2beach

Sea Whisper: North End Gem w/ Pool & Boat Dock

Lido Key Beach Bungalow with Private Heated Pool!

River Cottage 2/2 - Kayaks & Huge Deck-Old Florida

Anna Maria Cottage w/Golf Cart

Steps To The Beach, Private & Heated Pool, Renovat

Cottage by the Bay - free charging, Level 2 EV
Other vacation rentals with a kayak

Harbor Villa | Waterfront Pool & Spa | Firepit

Pool, Spa, Mini Golf, Games, Beach 4 bed 4 bath

Cedar Sunsets-4 bed, 4 bath, 4 Houses to the beach

Luxury-Incredible Views of Sunsets, Marina

Iris-istible Options by Beach Boutique Rentals

Sunswept Villa 4 - Waterview! 15 min to AMI beach

Nautic Star - Large pool & Waterfront & kayaks

Birds and Sunsets
When is the best time to visit Holmes Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,223 | ﺩ.ﺇ 1,612 | ﺩ.ﺇ 1,777 | ﺩ.ﺇ 1,491 | ﺩ.ﺇ 1,462 | ﺩ.ﺇ 1,697 | ﺩ.ﺇ 1,351 | ﺩ.ﺇ 900 | ﺩ.ﺇ 834 | ﺩ.ﺇ 867 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 1,003 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
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