Beach Living & Shuffleboard
16100 2nd St - Web Quality (4)
Full-Equipped Kitchen for making family meals
16100 2nd St - Web Quality (22)
Backyard

She's A Shore Thing

3 bedrooms·2 baths
Redington Beach • Florida

$1,145.96 USD $1,069.47 USD total for 3 nights

Oct 21 – 24, 2026

Property grounds
Living area
Private kitchen
Outdoor dining
Living area

Beachfront Condo at La Contessa!, 3BD/3BA, Poolside Cabana, Private Fishing Pier

3 bedrooms·3 baths
Redington Beach • Florida
5(12 reviews)

$11,215.25 USD total for 30 nights

Nov 15 – Dec 15, 2026

Casa Noir by Perez Benitez image 1
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Casa Noir by Perez Benitez image 5

Casa Noir by Perez Benitez

4 bedrooms·2 baths
St. Petersburg • Florida
5(6 reviews)
$300/ night(excl. fees & taxes)
Private screened pool with lounge chairs and easy indoor-outdoor access
Primary bedroom — king bed with coastal luxury bedding, wall-mounted smart TV, and direct sliding glass door access to the private screened pool.
Coastal dining room at Sun Oasis — a farmhouse-style table set for six with blue place settings and teal glassware, teal front door visible beyond, flowing into the living room.
Full living room — two plush sofas, striped armchair, coastal round ottoman, oversized Oasis on 40th turtle 70-inch TV art, guest book on the coffee table, and the game room archway beyond.
Screened private pool with string lights for relaxing evening swims

Sun Oasis Heated Pool Game Room and Wood Fire Pit Near St Pete Beaches

3 bedrooms·2 baths
St. Petersburg • Florida
5(72 reviews)

$683.64 USD $635.28 USD total for 3 nights

Oct 19 – 22, 2026

Beachside Blue Retreat | Walk to Beach | Long-Term
Beachside Blue Retreat | Walk to Beach | Long-Term
Beachside Blue Retreat | Walk to Beach | Long-Term
Beachside Blue Retreat | Walk to Beach | Long-Term
Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

1 bedroom·1 bath
Madeira Beach • Florida

$567.00 USD total for 3 nights

Oct 19 – 22, 2026

Blue Tide Retreat | Walk to Beach | Sleeps 4
Blue Tide Retreat | Walk to Beach | Sleeps 4
Blue Tide Retreat | Walk to Beach | Sleeps 4
Blue Tide Retreat | Walk to Beach | Sleeps 4
Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

1 bedroom·1 bath
Madeira Beach • Florida

$567.00 USD total for 3 nights

Oct 19 – 22, 2026

Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

4 bedrooms·2 baths
St. Petersburg • Florida
4.95(43 reviews)

$7,524.00 USD total for 30 nights

Oct 23 – Nov 22, 2026

Common Area: 🌳 Spacious Outdoor w/ table and chairs
Welcome to your perfect retreat—ideal for a solo traveler or couple.
St. Petersburg, Florida – a vibrant city bursting with sunshine, culture, and endless possibilities! Nestled on the Gulf Coast, St. Pete is a haven for art lovers, outdoor enthusiasts, and those seeking a laid-back coastal escape
A beautifully remodeled bathroom guests love.
Step outside to your private outdoor deck, complete with a dining table and chairs—perfect for morning coffee or alfresco meals in the fresh air.

Private Deck • Pet Friendly • Spacious Courtyard

0 bedrooms·1 bath
St. Petersburg • Florida

$427.14 USD total for 3 nights

Oct 19 – 22, 2026

Common Area
Common Area: 🌳 Spacious Outdoor w/ table and chairs
Private Deck • Pet Friendly • Spacious Courtyard
Private Deck • Pet Friendly • Spacious Courtyard
Private Deck • Pet Friendly • Spacious Courtyard

Private Deck • Pet Friendly • Spacious Courtyard

0 bedrooms·1 bath
St. Petersburg • Florida

$449.74 USD total for 3 nights

Oct 19 – 22, 2026

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR
Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR
Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR
Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR
Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

7 bedrooms·7 baths
Madeira Beach • Florida

$4,477.06 USD total for 3 nights

Oct 19 – 22, 2026

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

2 bedrooms·2 baths
Madeira Beach • Florida

$1,539.06 USD total for 3 nights

Oct 19 – 22, 2026

King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath
Madeira Beach • Florida

$1,380.16 USD total for 3 nights

Oct 19 – 22, 2026

Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

1 bedroom·1 bath
Madeira Beach • Florida

$1,253.04 USD total for 3 nights

Oct 19 – 22, 2026

King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath
Madeira Beach • Florida

$1,298.44 USD total for 3 nights

Oct 19 – 22, 2026

King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

1 bedroom·1 bath
Madeira Beach • Florida

$1,298.44 USD total for 3 nights

Oct 19 – 22, 2026

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 1
1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 2
1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 4
1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 5
1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 6

1Bedroom/ 10 mins to Downtown Saint Peterburg

1 bedroom·1 bath
St. Petersburg • Florida
4.36(25 reviews)
$85 – $95/ night(excl. fees & taxes)
Private studio/pets friendly/10 mins to Downtown
Private studio/pets friendly/10 mins to Downtown
Private studio/pets friendly/10 mins to Downtown
Private studio/pets friendly/10 mins to Downtown
Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

0 bedrooms·1 bath
St. Petersburg • Florida
4.32(19 reviews)

$316.00 USD total for 3 nights

Oct 19 – 22, 2026

Magnolia near the beach and downtown St. Pete image 1
Magnolia near the beach and downtown St. Pete image 2
Magnolia near the beach and downtown St. Pete image 3
Magnolia near the beach and downtown St. Pete image 4
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Magnolia near the beach and downtown St. Pete

5 bedrooms·3 baths
St. Petersburg • Florida
4.85(150 reviews)

$746.11 USD total for 3 nights

Oct 19 – 22, 2026

Mermaid Manor. Only 2 block to the BEACH!
Mermaid Manor - Waterfront | Dolphins & Sunsets
Mermaid Manor - Waterfront | Dolphins & Sunsets
Mermaid Manor - Waterfront | Dolphins & Sunsets
Mermaid Manor - Waterfront | Dolphins & Sunsets

Mermaid Manor - Waterfront | Dolphins & Sunsets

2 bedrooms·2 baths
Treasure Island • Florida

$699.78 USD total for 3 nights

Oct 19 – 22, 2026

Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views

Funshine Pointe Capri - Newly Renovated - Intercoastal Views

1 bedroom·1 bath
Treasure Island • Florida
5(178 reviews)

$453.66 USD total for 3 nights

Oct 19 – 22, 2026

Prime location, Pool Oasis near St. Pete Beach
Prime location, Pool Oasis near St. Pete Beach
Prime location, Pool Oasis near St. Pete Beach
Prime location, Pool Oasis near St. Pete Beach
Prime location, Pool Oasis near St. Pete Beach

Prime location, Pool Oasis near St. Pete Beach

2 bedrooms·2 baths
St. Petersburg • Florida
5(39 reviews)

$1,501.25 USD total for 3 nights

Oct 19 – 22, 2026

The Beautiful Treasure
The Beautiful Treasure
The Beautiful Treasure
The Beautiful Treasure
The Beautiful Treasure

The Beautiful Treasure

2 bedrooms·1 bath
St. Petersburg • Florida
5(26 reviews)

$1,224.35 USD $909.53 USD total for 7 nights

Nov 9 – 16, 2026

FREE heated swimming Pool. SPA does not have a jet pump.
Large Heated Pool
4 bikes are provided with Helmets. 2 adults and 2 kids bike.
Garage game room. w/foosball table, pingpong, easel for kids
beach umbrellas, beach chairs and coolers are provided.

FREE Pool Heating! Pet-Friendly!!!SPECIAL PRICING 04/13-04/30 ONLY!!!

3 bedrooms·0 baths
Palm Harbor • Florida

$642.00 USD total for 3 nights

Oct 19 – 22, 2026

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The Corner Cottage

2 bedrooms·1 bath
Palm Harbor • Florida
4.94(18 reviews)

$620.00 USD $595.25 USD total for 3 nights

Oct 19 – 22, 2026