Bay Dreamin Vacation Rental: 4 Bedroom Home With Heated Pool & Spa

Home Rental in Anna Maria Florida

Step onto the beachfront and you'll understand why guests keep coming back — the sand, the sky, and the water are all right there.

Your private pool is waiting. Grab a lounger, drop your drink in the holder, and let the afternoon blur into evening.

Waterfront vacation rental in Anna Maria, FL with four bedrooms, bay views of the Sunshine Skyway Bridge, a heated pool and spa, and Bayfront Park and beach access across the street near Pine Ave.

Book Direct

Anchor Down Vacation Rentals

Connect directly with the local vacation rental manager.

Rates from

$500 / night

Additional fees may apply

Book Direct

Bay Dreamin is a 4-bedroom, 3 full-bath, 2 half-bath waterfront home in Anna Maria, Florida that sleeps up to 8. Set at the tip of Anna Maria Island, it offers on-the-beach access across the street and water views from private outdoor spaces. A private heated pool and spa, plus features like a backyard putting green and outdoor wet bar, help balance beach time with at-home downtime.

The home has a two-story, stairs-only layout with the open living, kitchen, dining area, and a half bath on the main level, and all bedrooms upstairs in a split floor plan. Tech and entertainment include smart TVs in every bedroom, a 65" smart TV in the living room, and an additional upstairs family room. The updated kitchen includes a wine cooler, Keurig and drip coffee maker, and stainless-steel appliances. A dedicated laundry room with washer/dryer and an extra half bath is accessed from the pool area. Parking is available for up to four vehicles, with on-site golf cart charging; boat and trailer parking are not available.

Good fit for

Family Vacations

Waterfront setting Located at the tip of Anna Maria Island with open-water views.

On-the-beach access Beach access is directly across the street.

Private pool and spa Private heated pool and spa with pool heat included.

Two-story layout Main living areas downstairs; all four bedrooms are upstairs (stairs-only).

Parking and charging Parking for up to 4 vehicles with on-site golf cart charging.

Waterfront - OceanLocation Setting

On the BeachBeach Access

4 BedroomsBedrooms

3 Full, 2 Half BathroomsBathrooms

Sleeps 8Guest Capacity

2778 sq. ft.Living Space

Pool (Private)Pool

Sauna / Steam RoomHot Tub

Internet AccessInternet

TelevisionTelevision

YesAir Conditioning

YesWasher / Dryer

Anna Maria Florida

305 North Bay Boulevard, Anna Maria Florida 34216

Location & nearby Explore the Area

Bay Dreamin sits at the tip of Anna Maria Island in Anna Maria, Florida, where the street ends at open water. Beach access and Bayfront Park are directly across the street, and the home’s decks and balcony are positioned for bay views, including views of the Sunshine Skyway Bridge. Pine Ave is listed as 0.3 miles away for shopping, dining, and fishing. A free island trolley stop is one block from the house for getting around the island.

Anna Maria Vacation Rentals Sandbar Seafood & Spirits in Anna Maria Florida Bean Point Beach Bayfront Park Beach

Rates from

$500 per night

Check current rates & availability

Live booking details are maintained by Anchor Down Vacation Rentals.

Check Availability

Season	Nightly	Weekly	Monthly
November 2026 Nov 01, 2026 - Nov 19, 2026	$700	n/a	n/a
Thanksgiving 2026 Nov 20, 2026 - Nov 28, 2026	$1,999	n/a	n/a
November 2026 Nov 29, 2026 - Nov 30, 2026	$700	n/a	n/a
December 2026 Dec 01, 2026 - Dec 17, 2026	$500	n/a	n/a
Christmas 2026 Dec 18, 2026 - Jan 03, 2027	$2,999	n/a	n/a
January 2027 Jan 04, 2027 - Jan 31, 2027	$1,250	n/a	n/a
February 2027 Feb 01, 2027 - Feb 28, 2027	$1,500	n/a	n/a
March 2027 Mar 01, 2027 - Apr 17, 2027	$2,000	n/a	n/a
April 2027 Apr 18, 2027 - Apr 30, 2027	$2,000	n/a	n/a
May 2027 May 01, 2027 - May 31, 2027	$750	n/a	n/a
June 2027 Jun 01, 2027 - Jun 30, 2027	$850	n/a	n/a
July 2027 Jul 01, 2027 - Jul 31, 2027	$650	n/a	n/a
August 2027 Aug 01, 2027 - Aug 31, 2027	$600	n/a	n/a
September 2027 Sep 01, 2027 - Sep 30, 2027	$500	n/a	n/a
October 2027 Oct 01, 2027 - Oct 31, 2027	$500	n/a	n/a
November 2027 Nov 01, 2027 - Nov 18, 2027	$700	n/a	n/a
Thanksgiving 2027 Nov 19, 2027 - Nov 27, 2027	$1,999	n/a	n/a
November 2027 Nov 28, 2027 - Nov 30, 2027	$700	n/a	n/a
December 2027 Dec 01, 2027 - Dec 16, 2027	$500	n/a	n/a
Christmas 2027 Dec 17, 2027 - Jan 08, 2028	$2,999	n/a	n/a

Bay Dreamin is a recently renovated, 2,778-square-foot waterfront home on Anna Maria Island with four bedrooms and five bathrooms total (three full and two half). The setting places you at the end of the street facing open water, with beach access and Bayfront Park directly across the street. For time at home, the outdoor area includes a private heated pool and spa (pool heat included), a putting green, hammock, grill, and a covered porch with a wet bar and seating.

Inside, the layout is stairs-only and spans two levels. The main floor is organized around an open-concept living room, kitchen, and dining area, plus a half bath. All four bedrooms are upstairs in a split plan, with the primary suite on one side and three additional bedrooms with two shared bathrooms on the other. There is also an upstairs family room.

Sleeping options include a king primary suite with an ensuite bathroom featuring a freestanding soaking tub and glass-enclosed rain shower; two queen bedrooms; and a twin-over-full bunk bedroom with an ensuite bathroom. An upstairs common area includes a sleeper sofa for additional flexibility. Linens and bath and beach towels are provided.

For connectivity and entertainment, the home offers high-speed Wi-Fi, smart-lock self check-in, and smart TVs throughout, including a 65" TV in the main living room and a large outdoor TV by the pool. The kitchen is equipped with stainless-steel appliances, a wine cooler, Keurig and drip coffee maker, plus essentials such as a blender and toaster. Parking is limited to four vehicles; the garage is accessible but not used for vehicle parking, and no boat or trailer parking is available. Pets are not allowed.

Bay Dreamin By Anchor Down Vacation Rentals 
Wake up to open water and views of the Sunshine Skyway Bridge from your own private deck at the tip of Anna Maria Island. This fully renovated retreat pairs a heated pool and spa with a backyard putting green, so lazy mornings and playful afternoons both have a place to happen. It's the kind of Anna Maria Island vacation rental that makes you want to skip the dinner reservation and just stay home.
<h1 style="margin-top:20px; margin-bottom:10px">Highlights</h1>
⚓Beach access and Bayfront Park directly across the street 
⚓Just 0.3 miles to Pine Ave for shopping, dining, and fishing 
⚓Private heated pool and spa, with pool heat included in your rental rate 
⚓Backyard putting green, a hammock, and an outdoor wet bar for easy entertaining 
⚓Free island trolley one block away — explore without ever needing the car 
⚓Smart TVs throughout, including a 65" in the main living room 
⚓High-speed Wi-Fi and a smart lock for easy self-check-in 
⚓Fully stocked kitchen with a wine cooler, Keurig, and drip coffee maker 
⚓Beach gear included — chairs, wagon, cooler, and umbrella 
⚓Pack N Play available for the littlest guests 
⚓Parking for up to 4 vehicles, plus golf cart charging available on-site

<h1 style="margin-top:20px; margin-bottom:10px">Location</h1>
"Bay Dreamin" sits at the tip of Anna Maria Island, where the street ends at open water. Beach access and Bayfront Park are directly across the street, giving you a front-row spot for sunsets over Tampa Bay and views of the Sunshine Skyway Bridge. Pine Ave — with its shops, restaurants, and fishing spots — is just 0.3 miles away, and the free island trolley stops a block from the house, so you can explore Anna Maria, Holmes Beach, and Bradenton Beach without ever worrying about parking or traffic. Upstairs, a private balcony puts those same bay views just outside your door for a quieter look at the water.

<h1 style="margin-top:20px; margin-bottom:10px">Property & Access</h1>
This recently renovated home is a stairs-only, two-story layout: the open-concept living room, kitchen, dining area, and a half bath are all on the main level, and all four bedrooms are upstairs in a split floor plan, with the master suite on one side and three additional bedrooms and two shared bathrooms on the other. Parking is available for up to 4 vehicles, plus golf cart charging on-site; the garage is accessible but not used for vehicle parking, and boat and trailer parking are not available on-site.

<h1 style="margin-top:20px; margin-bottom:10px">Tech & Entertainment</h1>
Every bedroom comes with its own smart TV, plus a 65" smart TV in the downstairs living room and 55" smart TVs in both the master suite and the upstairs family room — plenty of screens for movie nights or catching the game. High-speed Wi-Fi keeps everyone connected, and a smart lock makes self-check-in simple the moment you arrive. Outside, a large flat-screen TV by the pool means the fun doesn't have to stop when you head outdoors.

<h1 style="margin-top:20px; margin-bottom:10px">Kitchen & Comfort</h1>
The updated kitchen is ready for a crowd, with new stainless-steel appliances, a wine cooler for your favorite beverages, and both a Keurig and a drip coffee maker to start the morning right, plus a blender and toaster for smoothies and quick breakfasts. The dining table seats 4, with additional bar seating at the kitchen island for overflow, and outside, a covered porch with a wet bar and a second seating area makes it easy to spread out for meals. Every bed is topped with fresh linens, and plush bath and beach towels are provided so you can head straight for the water. A dedicated laundry room with a washer, dryer, and its own half bath keeps mid-trip laundry out of the way. This is located in the garage and accessible from the pool. 

<h1 style="margin-top:20px; margin-bottom:10px">Room-by-Room</h1>
Bedroom 1: King bed, ensuite bathroom with a freestanding soaking tub and glass-enclosed rain shower, Smart TV 
Bedroom 2: Queen bed, shared bathroom, Smart TV 
Bedroom 3: Queen bed, shared bathroom, Smart TV 
Bedroom 4: Twin-over-Full bunk bed, ensuite bathroom, Smart TV 
Additional sleeping: Upstairs common area, sleeper sofa

<h1 style="margin-top:20px; margin-bottom:10px">Notes</h1>
*No pets allowed 
*Parking limited to 4 vehicles; no boat or trailer parking on-site 
*Pool heat is included in your rental rate; pool heaters are locked and monitored by the pool company with a maximum setting of 85°F — expect pool temperatures around 76°F during winter months, and note that cold snaps may slow heating time 
*A nightly damage waiver fee covers up to $1,500 in accidental damage as long as it's reported before checkout; see the Rental Agreement on the checkout page for full details 
 
Damage Waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee (“Management”), plus tax if applicable (the “Damage Waiver”). 
The Damage Waiver covers you for up to $1,500 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit. 
More information can be downloaded from the “Rental Agreement” on the checkout page.

This property provides access to the following activities and special interests:

Golfing

Biking

Fishing

Hiking

Scuba Diving

Sailing

Skiing

Surfing

Wind Surfing

Kayaking

Luxury

Beach

Horseback Riding

Boating

Family Vacations

Spa

Casino

Canoeing

Fly Fishing

Deep Sea Fishing

Ocean

Suitability

Children Welcome

Property Features

Ceiling Fan(s)

Refrigerator

Microwave

Dishes/Utensils

Stove

Toaster

Oven

Freezer

Parking

Garage

Phone

Hair Dryer

Iron / Ironing Board

Towels/Linens

Elevator

Balcony

Sauna / Steam Room

Featured Amenities

Air Conditioning

Television

Dishwasher

Grill

Internet Access

Fireplace

Washer/Dryer

Pool (Private)

Hot Tub

Entertainment

Movies

Video Games

Ping Pong Table

DVD Player

Game Room

Outdoor

Bicycle

Garden

Kayak/Canoe

Other Property Amenities

Laptop Friendly

Coffee Pot

Kettle

Self Check-In

Private yard

Beach Essentials

Bay Dreamin is located in Anna Maria, Florida.

Bay Dreamin accommodates up to 8 guests.

4 Bedrooms and 3 Full, 2 Half Bathrooms.

The listed beach access for Bay Dreamin is On the Beach.

Yes. The property lists Pool (Private).

Yes. The property lists Sauna / Steam Room.

Local management

Professionally Managed By

Anchor Down Vacation Rentals View Manager Profile

Book Direct View 74 Rentals

Contact Reservations and Guest Services at Anchor Down Vacation Rentals

Daytime Phone

Property reference

#193262 · Bay Dreamin

More rentals from the same manager, prioritized by location, property type, size, and setting.

Soak up the sun right outside your back door — heated pool, hot tub, lounge chairs, and swaying palms all yours for the week.

Hammock Hideaway 3 BR · Sleeps 7 · Home Rates from $425/day

Base House on Pine Ave 2 BR · Sleeps 4 · Condo Rates from $175/day

Mermaid Villa 3 BR · Sleeps 10 · Home Rates from $199/day

Cortez Cabana 5 BR · Sleeps 14 · Home Rates from $450/day

Casa Palma 4 BR · Sleeps 8 · Home Rates from $250/day

Swaying Palms 4 BR · Sleeps 8 · Home Rates from $199/day

Bay Dreamin Vacation Rental: 4 Bedroom Home With Heated Pool & Spa

Home Rental in Anna Maria Florida

Why You'll Love This Rental

Property Highlights

Rates & Availability (USD)

Availability Calendar

About This Rental

Activities and Special Interests