
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.
LocationOutdoor spacesCleanliness

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
Outdoor spacesLocationGrill

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.
LocationGetting aroundIndoor spaces

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.
Outdoor spacesLocationHospitality

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.
LocationValueBeach

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.
LocationOutdoor spacesDecor

Bay Breeze Cottages #2
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.
LocationValueFamily

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.
Outdoor spacesLocationAmenities

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.
LocationDecorHospitality

Dolphin Cove Waterfront St. Pete Beach w/ Pool
THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!
ValueLocationGetting around

ami skyview
When you open your door and step out, you will enjoy your own private white sandy beach, with sparkling blue/green, Gulf/Bay water. The location and view are incredible, only a blocks walk, to the famous Anna Maria City Pier, Pine Avenue, restaurants boutiques and shops. Enjoy kayaks, paddle boards and bicycles, all FREE, for our guests. Come and enjoy paradise! There is only one camera located at the front entrance (street side).
ValueOutdoor spacesGetting around

Las Palmas Beach Rentals unit 2
Ground floor; limited beach view . Steps to the white sandy beach. Free parking to registered guest. Furnished rooms, full size kitchen, linens provided. Free trolley stop on the block. GREAT LOCATION! Shopping and restaurants short walking distance. Check out our guidebook for additional island tips. Once booked it will be in your itinerary.
Outdoor spacesLocationPets
Popular amenities for Holmes Beach kayak rentals
House rentals with a kayak

Hibernate in our Bear Creek Home
ValueLocationLaundry

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

Historic Wares Creek 3 bedroom with dock access
LocationOutdoor spacesLong stay

Boat Dock + Kayaks + Dolphins + Beaches + Hot tub!
ValueLocationFamily

1918 Historic Cottage • Walk/Bike to AMI Beaches
LocationOutdoor spacesComfort

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

200 steps to the Beach | Heated pool + spa
Outdoor spacesValueIndoor spaces

Luxury Home-Canal-Pool-Kayak-Kingfisher Cay
LocationOutdoor spacesPool
Cottage rentals with a kayak

Sunny PaG Island rental w/bikes-just steps2beach
Outdoor spacesValueParking

Waterfront Villa Delphina
LocationAccuracyBeach

Anna Maria Cottage w/Golf Cart
LocationFamilyKitchen

Lido Key Beach Bungalow with Private Heated Pool!
LocationOutdoor spacesCheckout

Steps2Beach-Walk everywhere-Bikes & gear Included
Outdoor spacesValueDecor

River Cottage 2/2 - Kayaks & Huge Deck-Old Florida
Outdoor spacesLocationGetting around

1839 2 Bedroom

Sea Whisper: North End Gem w/ Pool & Boat Dock
ValueLocationKitchen
Other vacation rentals with a kayak

Waterfront 5BR w/Pool, Spa, Boat Lift, Putting Grn
Outdoor spacesLocationCheckout

The Lazy Turtle ~ Canal-Front Retreat
Outdoor spacesLocationFamily

Midnight Gulf Resort A
BeachWalkability

Gorgeous Canalfront Home w/ Dock | Walk to Beach!
Outdoor spacesValueBeach

Coconut Cove: *Canalfront *Pet-friendly *Putt-putt
Outdoor spacesLocationHot tub

Tranquil Bay: Waterfront Home w/ Heated Pool
ValueLocationNearby

Family Fun Heated Pool, Games, Crib, Peloton
Outdoor spacesLocationView

“Topside” luxury home in Cortez Village
LocationComfortCheck-in
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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