
Holiday rentals with a pool in Anna Maria
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Anna Maria

Total holiday rentals
Explore 430 holiday rentals in Anna Maria

Nightly prices starting at
Anna Maria holiday rentals start at $18 NZD per night before taxes and fees

Verified guest reviews
Over 8,020 verified reviews to help you choose

Family-friendly holiday rentals
410 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 150 rentals that welcome pets

Rentals with dedicated workspaces
260 properties have a dedicated workspace

Wi-Fi availability
430 of Anna Maria holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Anna Maria rentals

4.8 Average rating
Anna Maria stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Anna Maria
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Limited Availably w/ Private Boat Dock & 30' Pool
✨ 4.95★ GUEST FAVORITE! Canal Front & 1/2 Block to Beach Experience the ultimate AMI getaway! This 4.95-star tropical oasis features a wide canal with a 30' boat/fishing dock, a massive 16'x30' private pool, and is just a 1/2 block to the beach. Walk to everything:• 3-min walk to Bay Beach, 15 to Bean Point• Steps to Pine Ave shopping & City Pier• Stroll to Waterfront Restaurant & Two Scoops. Bring your boat, lounge poolside, or hit the sand. Perfect island living with 200+ rave reviews!

Beautiful Beach house! Heated pool and spa!
Discover your dream getaway at this beautifully decorated vacation rental in Anna Maria Island. This stunning 4-bedroom, 4.5-bathroom home offers luxury and comfort, featuring a spacious open-concept living area, modern kitchen, and elegant furnishings. Enjoy the private pool and hot tub, and the beach is just a 5-minute walk away. The highlight is the rooftop deck, where you can soak in breathtaking sunsets. Experience the perfect blend of style and convenience for your unforgettable vacation!

Green Jacaranda /Bean Point Beach 5 min walk/pool
Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

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.

Heated Pool, Hot Tub, Game Room, Steps to Beach!
Welcome to Island Dreams, the ultimate peaceful escape just 4 min walk from Anna Maria Island's stunning beaches. This fully renovated three-bedroom, three-bath beach house features a Zen-inspired backyard oasis, a private cocktail pool, and a game room! Walk to shops, restaurants, and the trolley stop! Island Dreams offers the perfect blend of relaxation, location, and indoor and outdoor fun! NOTE: Holmes Beach has a 7-day rental minimum. Check in / Check out days are on Saturdays.

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

Beach House w/Private Pool & Spa
Adorable beach cottage on the north end of Anna Maria Island! The beach access trail to the beautiful beach is right by the house. This 3 bedroom 2 bathroom home is situated on a corner lot on a quiet street and is located just steps to the beaches of the Gulf of Mexico. Enjoy the private pool and spa, surrounded by tropical landscaping. Tons of beach gear included! It is located in a great area to explore by bike, ride to Pine Ave., Bayfront Park, the City Pier, etc....

Pool & Sand Volleyball | 3 Kings | Near AMI & IMG
Escape to Two Palms, a spacious 4-bedroom, 3-bath retreat in Bradenton, Florida. Perfectly located just minutes from the sugar-sand beaches of Anna Maria Island. Designed with comfort and relaxation in mind, this home offers everything you need for a memorable getaway. Step inside to an open-concept living space filled with natural light and plenty of space to unwind. Outside, enjoy a private salt-water pool and a beach sand backyard featuring a sand volleyball court.

Ocean Air Oasis-New Centrally Located AMI Luxury
Immerse yourself in coastal luxury at this exceptional 3-bedroom, 2.5-bathroom custom home, where opulent high-end finishes and stunning pecky cypress floors adorn every nook. Revel in the impeccable features, including Sub-Zero and Wolf appliances, marble countertops, Shaw’s sinks, and exquisite custom woodworking, all bathed in abundant natural light. This delightful space offers panoramic views of the lavish backyard, complete with a heated pool and spa.

83rd St Villas East by Duncan Real Estate
Welcome to The 83rd St Villas East! A stunning ground-level vacation villa just a 6-minute walk from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. Top of the range, fully equipped kitchen with Café appliances, ample counter space, cook top and oven, extra-large fridge/freezer making meal prep a breeze.

Paradise on Pine
Welcome to "Paradise on Pine" – a stylish island retreat perfectly situated in the heart of Anna Maria! This charming 3-bedroom, 2-bath vacation home is nestled right on Pine Avenue – just 1.5 blocks to the stunning Gulf beaches and only a few blocks from the bay, City Pier, and all the boutique shops, eateries, and island favorites Anna Maria is known for. No need for a car – you’re just a flip-flop stroll to it all!

L'Oasis East w/Dip Pool
Completely remodeled, this beautifully 2-bedroom duplex, crafted to enhance your living experience. Every detail has been thoughtfully designed to create a serene and inviting atmosphere. New images showcase this stunning transformation, come visit us to see the beauty in person! Additionally, West and East are now available for rent together, featuring convenient adjoining doors through the utility room.
Popular amenities for Anna Maria rentals with a pool
House rentals with a pool

Ocean72 | Heated Pool & Spa | 2BR Near Beach

Bayfront Beach access with Heated Pool!

TOES IN THE SAND!

Waterfront w/ Dock + Mini Golf | Pool, Spa, Sauna

Americana AMI Lighthouse 3BR w/pool + rooftop deck

Lovin' the Sannd: North-end Cottage

Salt + Sol | Canal-Front | Golf Cart | Heated Pool

Bean Pt. Bungalow - Half duplex w/private pool
Condo rentals with a pool

Luxury 3/3 Margaritaville Resort

Beach Escape & Pool, steps to Beach & restaurants

Oceanfront Condo for Beach Lovers

AMI Perfect Experience

Island Time: Open July 7 - 10!

Steps to the beach! Condo with pool at The Terrace

Holmes Beach - literally a few steps to the beach

*Shore Thing* Walk to Beach | Intercoastal Views
Other holiday rentals with a pool

While Away A · EV Charger · Fenced Pool · Renovate

Getaway Family Beach Townhome w/Pool!

༄ Sunset Shore on Anna Maria Island ༄

Ocean Minded by Beach Boutique Rentals

Enjoy AMI sunsets | Chic home w/ Saltwater pool!

Home with heated pool, spa, games, walk to beach

Anna Maria retreat house

AMI Ohana Beach Resort B with fabulous salt pool!
When is the best time to visit Anna Maria?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $846 NZD | $1,100 NZD | $1,655 NZD | $1,156 NZD | $890 NZD | $1,010 NZD | $1,119 NZD | $816 NZD | $736 NZD | $702 NZD | $848 NZD | $937 NZD |
| 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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- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
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- Busch Gardens Tampa Bay
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Amalie Arena
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- Anna Maria Public Beach





