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Vacation rentals with a pool in Holmes Beach

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Quick stats about vacation rentals with a pool in Holmes Beach

  • Total vacation rentals

    Explore 1,110 vacation rentals in Holmes Beach

  • Nightly prices starting at

    Holmes Beach vacation rentals start at R 161 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 16,370 verified reviews to help you choose

  • Family-friendly vacation rentals

    990 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 350 rentals that welcome pets

  • Rentals with dedicated workspaces

    600 properties have a dedicated workspace

  • Wi-Fi availability

    1,110 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 rentals with a pool in Holmes Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
The living area features light-colored furniture with decorative pillows and wall art. Large windows allow natural light to fill the space, and a cooling ceiling fan is present. A decorative bowl rests on the low coffee table, complementing the warm wood flooring.
Home in Holmes Beach

New Golf cart + 4bd/3b w pool/2100 sq ft home

Urban Oasis is a privately owned 2100 sq ft 4 bd, 3 bth on Anna Maria Island. 4 minute walk on a quiet residential street to walk to the beach.This home features grey blue hues, coastal furniture, driftwood accents, themed rooms and designer accents. A brand new 2024 6 str golf cart is included in your rental as well as a premium linen service including all towels and linens. Urban Oasis is truly a turnkey Vacation Rental! We also have a second property, Urban Oasis Too, if you like our style!

4.88 out of 5 average rating, 129 reviews
Top guest favorite
Home in Holmes Beach

Waterfront, Heated Pool, Elevator, Fire Pit, Dock

Escape to The Blue Ark, a 3-story home inspired by Noah’s Ark. Families will love this peaceful retreat, blending luxury and comfort. Discover the island's only natural lagoon, boasting stunning views, manatee and occasional dolphin sightings! Unwind by the heated pool, fish from the dock, or take an easy 4-5 minute walk to the beach. End the day with a drink by the fire pit on the top deck, watching the sunset. The Blue Ark has an elevator, 3 bedrooms + extra sleep space, 8 beds and 4.5 baths.

5.0 out of 5 average rating, 65 reviews
Top guest favorite
Condo in Holmes Beach

Steps to the beach! Condo with pool at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

4.96 out of 5 average rating, 111 reviews
Top guest favorite
A sandy beach extends towards a calm ocean, where turquoise waters meet a clear blue sky. Colorful umbrellas provide shade for beachgoers, who are relaxing on vibrant towels. The shoreline features soft white sand, inviting visitors to enjoy the peaceful environment.
Townhouse in Holmes Beach

Getaway Family Beach Townhome w/Pool!

Wouldn't you like to get away?🌞 Just steps to the perfect family beach at this condo w/pool. Two bedrooms, two baths (+tub), sleeps six! King bed, queen w/twin bunk over, one convertible queen. Fresh updates: Washer-dryer, flooring, sofa, full kitchen, cable, wifi, beach toys, pack n play, baby gate. Did we mention the heated pool?🏊‍♀️ Next door to Walgreens, restaurants, bike rentals, shops, grocery. So many charming delights to discover on America's best beach, Anna Maria Island (AMI)!🏖

4.94 out of 5 average rating, 72 reviews
Top guest favorite
Condo in Holmes Beach

#terraceLIFE | 2 Blocks to Beach | Heated Pool

Escape to our cozy beachside retreat, steps from the sand! Retire the car in the garage, fill the wagon w/beach supplies & head to the shoreline at sunset. Spend time sipping coffee on 1 of the 3 balconies or cooling off in the pool w/the lush landscape. There's no better way to relax & enjoy AMI! Bedrooms on 2nd floor giving the main level separation. Sleeps 4-5 comfortably but can accommodate 6 w/sofa bed. Forgot something? Walgreens is right next door along with restaurants, shops & more!

4.88 out of 5 average rating, 112 reviews
Guest favorite
A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.
Home in Bradenton beach

Sea AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

4.96 out of 5 average rating, 212 reviews
Top guest favorite
A modern kitchen area features pale blue walls and a round dining table set for four. Stainless steel appliances, including a microwave and oven, are visible. A decorative light fixture made of translucent discs hangs above the table, adding a coastal touch to the space.
Condo in Holmes Beach

Short Stroll to the Surf! ~ Make Memories on AMI

Nestled in a charming, quiet community of just 8 units, this beautifully updated beach condo offers the perfect blend of relaxation and convenience. The condo is just a short stroll (about 150 steps!) to the pristine white sand beach, where you can soak up the sun and enjoy the coastal views. Wonderful family getaway or couples escape. Private, covered 2 car parking. Laundry in unit. Beach wagon, chairs and gear available. A hidden gem close to everything you need for a relaxing island stay.

4.99 out of 5 average rating, 159 reviews
Top guest favorite
An aerial view captures the coastal neighborhood, showcasing a collection of charming homes with grey rooftops. The vibrant blue ocean and sandy beach are visible in the background, while lush palm trees surround the area, contributing to the serene island atmosphere.
Townhouse in Holmes Beach

Steps from Beach! Heated Pool & Spacious Lanai!

Your Dream Beach Getaway! One block from the sugar-white sands of Holmes Beach, this freshly renovated coastal retreat is ready for your perfect island vacation! Cruise around on our free bikes, paddle our boards, or hit the beach with all the gear you need for a day in the sun. When it’s time to relax, take a dip in the shared, HEATED pool! At night, enjoy the laid-back charm of the Island. Explore local shops, delicious eats, and island vibes—all just a short bike ride from our home. .

4.98 out of 5 average rating, 172 reviews
Top guest favorite
A coastal view showcases a vibrant poolside area surrounded by lush greenery and palm trees. The inviting blue waters of the ocean are visible in the background, enhancing the outdoor space with a sunny, bright sky.
Apartment in Holmes Beach

Beachfront Anna Maria Island, Walk to Shops!

Pool is open!! Book today! Escape to paradise in this beautiful 3-bedroom, 2-bathroom vacation rental home located beach front from the white sandy beaches. The spacious living area is perfect for relaxing after a day at the beach, with comfortable seating and a large flat-screen TV. The kitchen is fully equipped with everything you need to prepare delicious meals. The master bedroom has a king-size bed, the second bedroom has a queen-size bed and the third bedroom with two full beds.

4.95 out of 5 average rating, 41 reviews
Top guest favorite
A private heated pool features a waterfall, surrounded by lush tropical landscaping and palm trees. Seating options include teal lounge chairs and white sunbeds, while the pool deck is complemented by a well-maintained lawn area. Colorful plants enhance the tranquil outdoor space.
Home in Holmes Beach

Salty Harbor AMI pool retreat near the Beach

Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our calendar! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

4.97 out of 5 average rating, 111 reviews
Top guest favorite
A heated pool is surrounded by lush greenery and palm trees. Lounge chairs are positioned along the perimeter, and a gentle blue hue reflects off the water. The two-story buildings in the background create a tranquil resort-like setting.
Condo in Holmes Beach

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean & comfortable. Sandy Pointe II is in a secluded setting, an easy walk to a less crowded, quieter section of beautiful AMI beach. Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! *NOTE- This unit is a walk-up, no elevator. 33 steps, spaced with 3 landings VRC # 20-000-272 Minimum stay 7 nights, Adult occupancy/4 , parking 2 vehicles & Quiet hours, 10 PM untill 7 AM

4.97 out of 5 average rating, 137 reviews
Top guest favorite
Home in Holmes Beach

NEW! w/ Pool - The Pearl Unit 2 on AMI

The Pearl (Unit 2) is a newly renovated oasis in the heart of Holmes Beach on Anna Maria Island. Just a 3–5 minute walk to the beach, this sunny AMI duplex home has everything — sparkling saltwater pool, fresh interiors, no stairs, beach gear, and parrots that may say hi on your morning walk! Centrally located and steps away from the AMI trolley to whisk you around the island! Relax, explore, and live your best island life. *pool is shared with one other unit in the duplex home*

5.0 out of 5 average rating, 11 reviews

Popular amenities for Holmes Beach rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
A private pool is surrounded by tropical landscaping, featuring a clear blue water surface that reflects soft lighting. Several lounge chairs are positioned nearby, providing relaxation space under the palm trees. The serene area is perfect for unwinding after a day at the beach.
Home in Anna Maria

Beach House w/Private Pool & Spa

4.96 out of 5 average rating, 107 reviews
Top guest favorite
Home in Anna Maria

Bean Pt. Bungalow - Half duplex w/private pool

5.0 out of 5 average rating, 108 reviews
Top guest favorite
Home in Bradenton Beach

Walk to it all! Restaurants + Heated Pool +Beach!

4.98 out of 5 average rating, 113 reviews
Top guest favorite
Home in Holmes Beach

Hidden Haven / Private Pool & Hot Tub

4.95 out of 5 average rating, 20 reviews
Top guest favorite
An aerial view showcases a spacious outdoor area featuring a private pool and lounge chairs, surrounded by a gated patio. A light blue house stands in the background with multiple windows, providing a connection between indoor and outdoor spaces. Lush greenery lines the property.
Home in Holmes Beach

Luxury 3BD Beachfront Retreat with Heated Pool!

4.94 out of 5 average rating, 47 reviews
Top guest favorite
A charming beach house is surrounded by lush palm trees and tropical landscaping. The exterior features a light blue color, and balconies are visible on the upper level. A paved pathway leads to the front entrance, creating an inviting approach.
Home in Holmes Beach

Anna Maria - 3 Bd 2 Bth-Heated Pool-Walk to Beach

4.95 out of 5 average rating, 63 reviews
Guest favorite
An aerial view showcases a coastal neighborhood with palm trees and sandy paths leading to the beach. The two-story home features a gray exterior and a deck visible on the side. The turquoise waters of the Gulf are seen in the background, enhancing the beach atmosphere.
Home in Holmes Beach

1 Block to Beach ~ 3BR Coastal Retreat with Pool

4.95 out of 5 average rating, 22 reviews
Guest favorite
An outdoor view showcases a private pool surrounded by lush landscaping and tropical palm trees. The distant beach features soft white sand meeting turquoise waters. A spacious deck, complete with loungers, offers a perfect relaxation spot under clear blue skies.
Home in Holmes Beach

TOES IN THE SAND!

4.9 out of 5 average rating, 73 reviews

Condo rentals with a pool

Guest favorite
A balcony offers a serene view of the Gulf of Mexico, featuring a lounge chair positioned for relaxation. The space is framed by a white railing, with sandy beach and greenery visible in the distance under a bright sky dotted with clouds.
Condo in Bradenton Beach

Oceanfront Condo for Beach Lovers

4.85 out of 5 average rating, 121 reviews
Guest favorite
A serene outdoor pool area is surrounded by lush tropical landscaping. The well-maintained pool is framed by the charming two-story buildings of the Palm Cay complex, with lounge chairs positioned nearby for relaxation. Palm trees sway gently in the warm sunlight.
Condo in Holmes Beach

1/1 STEPS to Beach w/ Heated POOL - Sleeps 4

4.94 out of 5 average rating, 143 reviews
Top guest favorite
A two-story yellow condo is highlighted against a clear blue sky. Palm trees line the pathway leading to a fenced pool area. The entrance features a covered balcony with white railings, offering a welcoming view of the surrounding tropical landscape.
Condo in Bradenton Beach

Beachy Chic! 1st Floor Condo-Pool-Close to Beach

4.92 out of 5 average rating, 125 reviews
Top guest favorite
The outdoor area features a heated pool with a rock waterfall, surrounded by lounge chairs. A thatched Tiki hut provides shaded seating, set within tropical landscaping. The villa's light blue exterior and white furnishings enhance the inviting atmosphere of the space.
Condo in Holmes Beach

Blanco at Sunset Villas on Anna Maria Island

4.93 out of 5 average rating, 160 reviews
Top guest favorite
A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.
Condo in Longboat Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

4.9 out of 5 average rating, 238 reviews
Guest favorite
Condo in Bradenton Beach

Cute 1Bedroom Beach condo, only steps from beach!

4.76 out of 5 average rating, 143 reviews
Superhost
A serene view from a balcony is presented, showcasing calm waters and lush greenery along the shoreline. Two wicker chairs and a round table are positioned on the balcony, enhancing the inviting outdoor space. The sky is clear, reflecting soft natural light on the water.
Condo in Bradenton Beach

Charming 2BD/2BR with Big Water Views on the beach

4.85 out of 5 average rating, 102 reviews
Top guest favorite
A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.
Condo in Longboat Key

Island Time!

4.98 out of 5 average rating, 253 reviews

Other vacation rentals with a pool

Guest favorite
Apartment in Holmes Beach

206 Cute 2 bed/1bath w/pool Steps to the Beach!

4.72 out of 5 average rating, 117 reviews
Top guest favorite
A coastal-style duplex is framed by lush tropical landscaping, featuring palm trees and colorful flowering plants. The exterior showcases light-hued siding, a spacious front porch with railings, and two garage spaces below. A clear blue sky enhances the inviting atmosphere of the property.
Cottage in Holmes Beach

Close to the Beach+ Private heated pool and spa!

4.95 out of 5 average rating, 83 reviews
Top guest favorite
A cozy bedroom features a spacious bed with light bedding, accented by decorative pillows. Natural light streams through sheer curtains by the window, illuminating the room's soft blue walls. A wooden dresser and a ceiling fan add functional elements to the friendly space.
Villa in Holmes Beach

Starfish House - 2bed/2bad

4.95 out of 5 average rating, 55 reviews
Guest favorite
Home in Holmes Beach

Beach Daze by Beach Boutique Rentals

4.9 out of 5 average rating, 29 reviews
Guest favorite
Home in Holmes Beach

Anna Maria retreat house

5.0 out of 5 average rating, 16 reviews
Guest favorite
A private heated pool, approximately 33 feet long, is surrounded by lush greenery. Covered in-pool seating and a small table are visible, along with a patio area featuring an outdoor shower and an umbrella-shaded dining table for six.
Home in Holmes Beach

Turtle Nest! Private Heated Pool & Walk to Beach!

4.88 out of 5 average rating, 17 reviews
Top guest favorite
Home in Holmes Beach

The Palace ~ Walk to Beach/Rooftop Views

5.0 out of 5 average rating, 14 reviews
Top guest favorite
A view from a private balcony showcases lush greenery, swaying palm trees, and vibrant flowers. The serene pool area is visible, along with the beach and ocean in the background under a partly cloudy sky.
Apartment in Holmes Beach

Breezy Beachside Views! Heated Pool & Pickleball!

4.96 out of 5 average rating, 47 reviews

When is the best time to visit Holmes Beach?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 4,993 ZARR 6,797 ZARR 8,907 ZARR 6,684 ZARR 5,782 ZARR 6,958 ZARR 5,798 ZARR 4,832 ZARR 4,365 ZARR 3,978 ZARR 4,558 ZARR 4,832 ZAR
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

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