House in Holmes Beach, FL
6 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
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
About this house rental
Welcome to Diamond Surf – Your Private Slice of Paradise on Anna Maria Island
What You’ll Love About This Home:
• Amazing Location! Just 1.2 blocks to the Gulf Beach and steps from the FREE island trolley
• No stairs – Convenient, ground-level living
• 2 Bedrooms / 2 Bathrooms / Bonus Family Room with Trundle Bed
• Sleeping for 6: 1 King, 1 Queen, 2 Twin Beds
• Private Heated Pool (heated Oct–Apr) surrounded by lush native palms
• Poolside Comfort: Lounge chairs, Adirondack chairs, dining area, umbrella
• Outdoor Shower + Gas Grill
• Fully Equipped Kitchen with gas range, dishwasher, drip coffee maker
• Smart TVs in all rooms + Complimentary WiFi
• Beach-Ready Gear: Towels, chairs, umbrella, toys & wagon
• 2-Car Driveway Parking
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Step Into Relaxation at Diamond Surf
Fall in love with Diamond Surf's charming "Old Florida" vibe—no stairs, just easy island living. Perfect for families, couples, or a small group of friends, our cheerful 2-bedroom, 2-bath home is your gateway to paradise.
You’re just a 3-minute walk to the powdery white sands of the Gulf of Mexico and a few steps from the free Anna Maria Island Trolley, which takes you to local favorites like Pine Avenue’s shops, restaurants, and cafes—including the beloved Ginny’s and Jane E’s.
When it’s beach time, simply load up the included beach wagon with towels, chairs, umbrella, and toys—and off you go!
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Inside the Home:
• Bedroom 1: King bed, adjacent bathroom, Smart TV
• Bedroom 2: Queen bed, en-suite bathroom, Smart TV
• Bonus Family Room: Twin trundle beds, Smart TV
The open-concept living space invites connection, whether you're making a meal in the fully equipped kitchen or relaxing on designer-inspired furnishings in the family room. Dine comfortably at the table for six, stay cool with central A/C, and stay connected with fast WiFi and Smart TVs.
For your convenience, there's a private washer and dryer, so you can pack light and wash as you go.
________________________________________
Outdoor Oasis:
The backyard is a true retreat. Take a dip in the private heated pool, nap in the shade, or dine under the stars. Enjoy:
• Weber gas grill
• Two outdoor dining areas
• Fenced yard with locking gate
• Outdoor shower
• Easy garage access for beach gear
________________________________________
Looking for More Space?
Check out our sister property, Sapphire Surf – another beautiful 2BR/2BA home just 5 blocks away. (VRBO Listing #394277)
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Secure & Simple:
Diamond Surf features a keyless digital lock—your personalized code is created just for your stay and reset afterward.
________________________________________
Our Promise to You:
We’re committed to providing a high-quality rental at a fair price. Our calendar is always up to date, and our rates are accurate. Just enter your dates and click “Book Now”
What You’ll Love About This Home:
• Amazing Location! Just 1.2 blocks to the Gulf Beach and steps from the FREE island trolley
• No stairs – Convenient, ground-level living
• 2 Bedrooms / 2 Bathrooms / Bonus Family Room with Trundle Bed
• Sleeping for 6: 1 King, 1 Queen, 2 Twin Beds
• Private Heated Pool (heated Oct–Apr) surrounded by lush native palms
• Poolside Comfort: Lounge chairs, Adirondack chairs, dining area, umbrella
• Outdoor Shower + Gas Grill
• Fully Equipped Kitchen with gas range, dishwasher, drip coffee maker
• Smart TVs in all rooms + Complimentary WiFi
• Beach-Ready Gear: Towels, chairs, umbrella, toys & wagon
• 2-Car Driveway Parking
________________________________________
Step Into Relaxation at Diamond Surf
Fall in love with Diamond Surf's charming "Old Florida" vibe—no stairs, just easy island living. Perfect for families, couples, or a small group of friends, our cheerful 2-bedroom, 2-bath home is your gateway to paradise.
You’re just a 3-minute walk to the powdery white sands of the Gulf of Mexico and a few steps from the free Anna Maria Island Trolley, which takes you to local favorites like Pine Avenue’s shops, restaurants, and cafes—including the beloved Ginny’s and Jane E’s.
When it’s beach time, simply load up the included beach wagon with towels, chairs, umbrella, and toys—and off you go!
________________________________________
Inside the Home:
• Bedroom 1: King bed, adjacent bathroom, Smart TV
• Bedroom 2: Queen bed, en-suite bathroom, Smart TV
• Bonus Family Room: Twin trundle beds, Smart TV
The open-concept living space invites connection, whether you're making a meal in the fully equipped kitchen or relaxing on designer-inspired furnishings in the family room. Dine comfortably at the table for six, stay cool with central A/C, and stay connected with fast WiFi and Smart TVs.
For your convenience, there's a private washer and dryer, so you can pack light and wash as you go.
________________________________________
Outdoor Oasis:
The backyard is a true retreat. Take a dip in the private heated pool, nap in the shade, or dine under the stars. Enjoy:
• Weber gas grill
• Two outdoor dining areas
• Fenced yard with locking gate
• Outdoor shower
• Easy garage access for beach gear
________________________________________
Looking for More Space?
Check out our sister property, Sapphire Surf – another beautiful 2BR/2BA home just 5 blocks away. (VRBO Listing #394277)
________________________________________
Secure & Simple:
Diamond Surf features a keyless digital lock—your personalized code is created just for your stay and reset afterward.
________________________________________
Our Promise to You:
We’re committed to providing a high-quality rental at a fair price. Our calendar is always up to date, and our rates are accurate. Just enter your dates and click “Book Now”
Amenities at AMI North End Private Heated Pool. 1.2 Block to Gulf Beach!
Non-smoking
No pets allowed
Map of Holmes Beach, FL
Ratings and reviews
Summary of reviewsGuests loved their stay at Diamond Surf with its great location, well-maintained property, clean interiors, fully equipped kitchen, comfortable pool area, and easy access to the beach.
10 / 10Outstanding·Feb 2026
Host was extremely responsive.
10 / 10Outstanding·Feb 2026
Perfect place for us!Loved the location- quiet dead end street away from the bustle of the commercial areas of Anna Maria and Holmes beach yet walkable plus the free trolley stop at the end of the street Also loved short walk to the beach (although crossing gulf can be a challenge when traffic is heavy). And the beach by the house is less crowded than public access areas. Loved the cleanliness of the house, everything in working order and everything we needed. The beach chairs, umbrella and wagon were in excellent working order and the back pack chairs were easy to carry and set up. Also loves the magnetic scrabble set on the wall. Loved the back yard. It was big, high privacy fence, nice heated pool and both sunny and shady areas to sit. Although the house is next to a church parking lot we did not hear any noise while sitting outside other than the traffic on gulf blvd. Didn’t love leaving but we will return next year.
10 / 10Outstanding·Jan 2026
I had a wonderful stay here. Place was nice and perfect location. Great communication with the owners. I would 100% book this house again and plan on it soon.
10 / 10Outstanding·Dec 2025
Excellent stay! The house had everything we needed. It was centrally located and the walk to the beach was so easy. We would definitely come again!
$$$$
Top rated by guests
9.9Outstanding
(154 Ratings)
Guests loved their stay at Diamond Surf with its great location, well-maintained property, clean interiors, fully equipped kitchen, comfortable pool area, and easy access to the beach.
From real guest reviews summarized by AIDon't miss out! Price and availability may change
