See all properties

Pineapple Key

Pineapple Key House in Holmes Beach

Pineapple Key House in Holmes Beach

Pineapple Key House in Holmes Beach

Pineapple Key House in Holmes Beach

Pineapple Key House in Holmes Beach

Don't miss out! Price and availability may change

House in Holmes Beach, FL

8 guests · 4 bedrooms · 2 baths

Reasons to book

High-end valueWell priced for this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Includes essentialsFree WiFi/internet and more

About this house rental

Pineapple Key is located in Holmes Beach, just a 2-minute walk from Anna Maria Island and 16 miles from Sarasota International Convention Center. This property offers a private pool, free Wifi, and free private parking.

Amenities at Pineapple Key

Free WiFi/internet

Free Parking

Non-smoking

Heating

WiFi/Internet

Map of Holmes Beach, FL

city location on map

Nearby attractions

St. Pete Pier™

Mote Marine Laboratory & Aquarium

Imagine Museum: Contemporary glass art

$$$$

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Pineapple Key. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Pineapple Key pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Pineapple Key?

We found 5 amenities for this rental. This includes free wifi/internet, free parking, non-smoking, heating, and wifi/internet.

Explore similar stays in Holmes Beach

Explore all stays

8.4 / 10.0

Excellent(426 Ratings)

Haley's at The Anna Maria Island Inn

in Holmes Beach

4 guests · 1 bedroom · 1 bath

Free WiFi/internet · Air conditioning · Pool

Discover the beauty of Holmes Beach with a stay at Haley's at The Anna Maria Island Inn, a top rated Apartment with amenities such as Non-smoking, Air conditioning and WiFi/Internet, and more.

Tropical Escape with Private Pool and Beach Proximity

in Holmes Beach

8 guests · 4 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

This Apartment in Holmes Beach, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

8.6 / 10.0

Excellent(426 Ratings)

Haley's at The Anna Maria Island Inn

in Holmes Beach

4 guests · 1 bedroom · 1 bath

Free WiFi/internet · Air conditioning · Pool

Looking for the perfect place to call home during your trip to Holmes Beach? This Apartment offers a comfort and style with top-notch amenities, including Non-smoking, Air conditioning and WiFi/Internet, and more.

Fish Stix - 110 - 72nd St

in Holmes Beach

10 guests · 1 bedroom · 5 baths

Free WiFi/internet · Pool · Hot tub/Jacuzzi

This House in Holmes Beach, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

9.4 / 10.0

Outstanding(33 Ratings)

Pool - Casa Del Mar by SeaBreeze Vacation

in Holmes Beach

8 guests · 4 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

This House for $401 in Holmes Beach, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

You can save with One Key

8.8 / 10.0

Excellent(3 Ratings)

Coco Cay - Beautiful totally remodeled 4 bedroom with private pool

in Holmes Beach

9 guests · 4 bedrooms · 4 baths

Free WiFi/internet · Air conditioning · Pool

Business stays, family stays, couples stay, getaway vacation, and rental in Holmes Beach at Coco Cay - Beautiful totally remodeled 4 bedroom with private pool for $403 for your next trip.

Island-style townhome only 460 steps to WOW of A beach

in Holmes Beach

8 guests · 3 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Washing machine

Looking for a House in Holmes Beach, this House for $394 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

Full Duplex, 5-minute walk to the Beach! - Gulf Haven

in Holmes Beach

8 guests · 4 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · TV

Are you ready to indulge in a relaxing getaway? Our House in Holmes Beach has everything you need for a rejuvenating stay. Treat yourself to Full Duplex, 5-minute walk to the Beach! - Gulf Haven's exceptional amenities, such as Air conditioning, Dryer and WiFi/Internet.

Key West Style Oasis on Anna Maria Island

in Holmes Beach

8 guests · 4 bedrooms · 3 baths

Air conditioning · Pool · Balcony/Terrace

Are you ready to indulge in a relaxing getaway? Our House in Holmes Beach has everything you need for a rejuvenating stay. Treat yourself to Key West Style Oasis on Anna Maria Island's exceptional amenities, such as Balcony/Terrace, Non-smoking and Family friendly.

Island-style townhome only 460 steps to WOW of A beach

in Holmes Beach

8 guests · 3 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Washing machine

This inviting House in Holmes Beach can fit your needs for many types of vacations, at $394 per night.

Island Breeze Balcony Escape

in Holmes Beach

8 guests · 4 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

Looking for a memorable stay in Holmes Beach? Our Apartment might just be what you're looking for. Enjoy amenities including Coffee/tea maker, Fire extinguisher and Private entrance, and more during your stay.

9.8 / 10.0

Outstanding(21 Ratings)

Under the Tuscan Sun: *Heated Pool *Close to Beach *Perfect Central Location

in Holmes Beach

10 guests · 3 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Holmes Beach, at $407 per night for your next great vacation.

8.0 / 10.0

Excellent(6 Ratings)

Villa Verde-4 bedroom with private pool with restaurants and boutiques nearby!!

in Holmes Beach

8 guests · 4 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

Enjoy the best of Holmes Beach in our House, Villa Verde-4 bedroom with private pool with restaurants and boutiques nearby!!. A stunning property with amenities including Air conditioning, Balcony/Terrace and Dryer, and more.

You can save with One Key

10.0 / 10.0

Outstanding(4 Ratings)

By the Sand cozy 3 story house Steps from the Sand of Holmes Beach.

in Holmes Beach

8 guests · 3 bedrooms · 2 baths

WiFi/Internet · Air conditioning · TV

When traveling to Holmes Beach, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $401 per night.

Buena Vista #2 - 101 - 67th Street #2

in Holmes Beach

8 guests · 1 bedroom · 4 baths

Free WiFi/internet · Pool · Hot tub/Jacuzzi

Experience the best of Holmes Beach with this House available for $338. This property is equipped with amenities including Free Parking, Gym and WiFi/Internet, and more.

10.0 / 10.0

Outstanding(43 Ratings)

Beach Lovers’ Pick: Ground-Floor 3-Bedroom, Patio & Pets

in Holmes Beach

8 guests · 3 bedrooms · 2 baths

Looking to create some memories in Holmes Beach? Look no further than our Apartment, Beach Lovers’ Pick: Ground-Floor 3-Bedroom, Patio & Pets. Enjoy top-rated amenities including Family friendly and Non-smoking, and more.

10.0 / 10.0

Outstanding(1 Rating)

Ychous Key Royale by Beach Boutique Rentals

in Holmes Beach

8 guests · 4 bedrooms · 4 baths

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Holmes Beach, at $386 per night for your next great vacation.

Tiki Paradise Poolside Escape

in Holmes Beach

8 guests · 4 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

Enjoy the best of Holmes Beach in our Apartment, La Mer. A stunning property with amenities including Air conditioning, Stove and Fire extinguisher, and more.

Mermaid's Haven, perfect getaway

in Bradenton Beach

8 guests · 3 bedrooms · 2 baths

Indulge in a peaceful retreat at Mermaid's Haven, perfect getaway, our elegant Apartment in Holmes Beach. Enjoy amenities including No pets allowed, Family friendly and Non-smoking, and more.

Private balconies, Walk to Holmes Beach, sleeps 8, access to heated pool

in Holmes Beach

8 guests · 3 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

This attractive Apartment in Holmes Beach, $393 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

Dolphin Tales - 836 S Bay

8 guests · 1 bedroom · 3 baths

Free WiFi/internet · Pool · Accessible by lift

Are you ready to indulge in a relaxing getaway? Our House in Holmes Beach has everything you need for a rejuvenating stay. Treat yourself to Dolphin Tales - 836 S Bay's exceptional amenities, such as Free Parking, Gym and WiFi/Internet.

9.8 / 10.0

Outstanding(21 Ratings)

Under the Tuscan Sun: *Heated Pool *Close to Beach *Perfect Central Location

in Holmes Beach

10 guests · 3 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

Experience the best of Holmes Beach with this House available for $407. This property is equipped with amenities including Air conditioning, Dryer and WiFi/Internet, and more.

You can save with One Key

10.0 / 10.0

Outstanding(43 Ratings)

Beach Lovers’ Pick: Ground-Floor 3-Bedroom, Patio & Pets

in Holmes Beach

8 guests · 3 bedrooms · 2 baths

Nestled in Holmes Beach, this Apartment is perfect for your next vacation. Enjoy Beach Lovers’ Pick: Ground-Floor 3-Bedroom, Patio & Pets's top-rated amenities, including Family friendly and Non-smoking, and more.

7.8 / 10.0

Good(11 Ratings)

Anthony Beach Cottages - Island Retreat Heated pool home w/ 4 bedrooms 3 baths

in Holmes Beach

8 guests · 4 bedrooms · 3 baths

WiFi/Internet · Air conditioning · Pool

Business stays, family stays, couples stay, getaway vacation, and rental in Holmes Beach at Anthony Beach Cottages - Island Retreat Heated pool home w/ 4 bedrooms 3 baths for $291 for your next trip.

Wading Pool Haven by the Beach

in Holmes Beach

8 guests · 4 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

The best choice in Holmes Beach for House, for $414 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

You can save with One Key

Private balconies, Walk to Holmes Beach, sleeps 8, access to heated pool

in Holmes Beach

8 guests · 3 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

This Apartment in Holmes Beach, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

Gulf Haven

in Holmes Beach

8 guests · 4 bedrooms · 2 baths

Free WiFi/internet

Are you ready to indulge in a relaxing getaway? Our House in Holmes Beach has everything you need for a rejuvenating stay. Treat yourself to Gulf Haven's exceptional amenities, such as Pets allowed, Golf course (within 2 mi) and WiFi/Internet.

8.0 / 10.0

Excellent(11 Ratings)

Anthony Beach Cottages - Island Retreat Heated pool home w/ 4 bedrooms 3 baths

in Holmes Beach

8 guests · 4 bedrooms · 3 baths

WiFi/Internet · Air conditioning · Pool

This inviting House in Holmes Beach can fit your needs for many types of vacations, at $291 per night.

9.8 / 10.0

Outstanding(42 Ratings)

Lazy Lagoon: On Canal, Pool, Boat Dock, 2 blocks to Beach by Anna Maria Life Vacation Rentals

8 guests · 4 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

House in Holmes Beach, for $1,231 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

9.8 / 10.0

Outstanding(43 Ratings)

Lazy Lagoon: On Canal, Pool, Boat Dock, 2 blocks to Beach by Anna Maria Life Vacation Rentals

8 guests · 4 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

This House for $1,231 in Holmes Beach, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)