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

Tropical Sunset 1 by SeaBreeze Vacation
Looking for the perfect beach destination? This 2 bedroom/2 bath condo, recently updated, is centrally located on Holmes Beach and is only steps from sparkling gulf waters and white sandy beaches. New floors, new furnishings and decor - this place is your coastal getaway! Plenty of natural lighting large windows in the living room, a screened in cozy balcony to enjoy your morning coffee or an evening cocktail, and a fully-equipped kitchen with new backsplash and countertops overlooking the pool.

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!

Be an 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.

Beautiful ground level with heated pool!
Escape to this cozy cottage on Holmes Beach, just a block from the beautiful shoreline! Perfect for families or couples, this inviting retreat features a comfortable living space and a fully equipped kitchen. Step outside to your private pool, perfect for cooling off after a day at the beach. Enjoy the tropical landscaping and outdoor seating area for relaxation. With the beach so close, you can easily indulge in sunbathing, swimming, and seaside strolls. Experience the charm of island living!

Poolside Oasis on Anna Maria Island!
Remodeled cottage with a lush tropical backyard, which boasts a Private Heated pool with Waterfall and Swim-up Tiki Table, turf putting green ,Weber Grill, patio bar with 55” Outdoor Smart TV! Calypso is outfitted with a cozy Coastal decor, you feel that vacation vibe as soon as you walk in the door. The kitchen offers quartz countertops with Stainless Steel appliances. Both bedrooms have King size beds, living room has a queen sleep sofa. All furniture was brand new in December of 2024

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

The Peachy Beach House, steps to the gulf
The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

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.

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI
Enjoy Florida sun in a stunning, newly renovated 4/2 pool home! We have provided almost everything we could think of including five 4k TVs w/ Netflix and cable, wifi, heated (optional) salt water pool w/ 7' privacy fencing, adult bikes, beach gear, Pack & Play, office, board games, relaxing lounge chairs, stocked kitchen, washer & dryer, garage parking, dog crate, all in a quiet and safe neighborhood. Oh, and of course it's just 5 miles to world renowned beaches.

Sunset and beach view from your balcony Unit 403
A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.

Captain's Quarters at Spinnakers Vacation Cottages
My place is close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love my place because of the high ceilings, the location, and the ambiance. It is located in the lush tropical paradise of Spinnakers Vacation Cottages. With a large living room, dining area and large master suite, it is perfect for couples, families (with kids), and furry friends (dogs, with a small pet fee). Captains Quarters also has Private patio!

A Coastal Retreat Steps From the Sea
Just a short walk to the sugary sands of Holmes Beach! This recently updated condominium has everything you need to enjoy a true getaway. Grab our beach chairs, umbrella, coolers, toys, and amazing beach cart to effortlessly pull the beach necessities across the sand. After a nice float in the ocean, come back to the tropical setting surrounding our heated pool. Welcome to Island Life.
Popular amenities for Holmes Beach rentals with a pool
House rentals with a pool

Blue Bungalow B

AMI Bridge Street Pier Phase Inn

Key Lime Cottage by Beach Boutique Rentals

Dolphin Resort | Pool, Spa, Game Room & Beach

Pickleball - Heated Pool - Relax, Play & Grill

Sunset View Pet Friendly w/Pool Beach Home

AMI Beach Villa, 3BR King family stay & Kayak

NEW! Steps to Private Beach, Heated Pool + Hot Tub
Apartment rentals with a pool

Steps from the beach

Anna Maria Island -walk to the beach!

Sandcastle Splash - Beachfront Condo

Beach Escape & Pool, steps to Beach & restaurants

Secluded Bayside Gem with beautiful bay views

Wander Residence - Fort DeSoto 2B/2B w/ Water View

Steps to the beach! Condo with pool at The Terrace

Vitamin Sea Escape: Open Wednesday!
Other holiday rentals with a pool

New! Luxurious Retreat w/ Resort Amenities by AMI!

100 yr Old Stone Home + Pool + 9 miles to beaches

Sand & Sea Oasis: Condo with Private Beach Access

Rated top 1% of all rentals on AMI! Heated pool!

Getaway Family Beach Townhome w/Pool!

pink peacock

Freshly Renovated Vacation Villa at Shorewalk

Beach getaway pool, spa, mini golf, walk to beach
When is the best time to visit Holmes Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 246 | € 312 | € 405 | € 325 | € 268 | € 304 | € 312 | € 260 | € 235 | € 214 | € 245 | € 260 |
| 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 |
Quick stats about holiday rentals with a pool in Holmes Beach

Total holiday rentals
Explore 1,150 holiday rentals in Holmes Beach

Nightly prices starting at
Holmes Beach holiday rentals start at € 9 per night before taxes and fees

Verified guest reviews
Over 14,600 verified reviews to help you choose

Family-friendly holiday rentals
1,020 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 370 rentals that welcome pets

Rentals with dedicated workspaces
610 properties have a dedicated workspace

Wifi availability
1,140 of Holmes Beach holiday rentals include wifi 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!
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