Family-Friendly Vacation Rentals in Crossroads Area, FL: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  USA

  4.  Florida
  5.  St. Petersburg - Clearwater
  6.  Crossroads Area

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2026 Best Family Vacation Rentals in Crossroads Area (Starting from $66)

Lovely St Petersburg Home with Backyard Oasis
Lovely St Petersburg Home with Backyard Oasis
House
St Petersburg, FL, USA
0.7k from Crossroads Area center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

2 Bedrooms4 Guests
New to Booking
$144
Average price / night
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3/2 Oasis w/ Private Heated Pool, Spa + Office. 8 Min to Beach. Pet Friendly!
3/2 Oasis w/ Private Heated Pool, Spa + Office. 8 Min to Beach. Pet Friendly!
House
St. Petersburg, FL, 33710, United States
0.3k from Crossroads Area center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$305
Average price / night
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3BR - Beach & Trail - Bikes, Fire Pit, Mini-Golf
3BR - Beach & Trail - Bikes, Fire Pit, Mini-Golf
House
St Petersburg, FL, USA
0.8k from Crossroads Area center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
8.5

Very Good

2 reviews

$354
Average price / night
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Flo's house III with private heated pool, 3 bedrooms and 3 bathrooms
Flo's house III with private heated pool, 3 bedrooms and 3 bathrooms
House
St. Petersburg, FL, 33710, United States
0.8k from Crossroads Area center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$346
Average price / night
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Bed and Bath in St Petersburg Home
Bed and Bath in St Petersburg Home
House
St. Petersburg, FL, USA
0.8k from Crossroads Area center

Accommodations, Parking, Homestays, Pet-friendly, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$66
Average price / night
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Trailside Home with Fun Game Yard
Trailside Home with Fun Game Yard
House
St. Petersburg, FL, 33710, United States
0.9k from Crossroads Area center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

27 reviews

$484
Average price / night
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St Petes Beach House 3BR 2 5BA Sleeps 8 Pool Pickleball Games BBQ
St Petes Beach House 3BR 2 5BA Sleeps 8 Pool Pickleball Games BBQ
House
St. Petersburg, FL, USA
1.1k from Crossroads Area center

Internet, Sports/Activities, View, Air Conditioner, Pet Friendly, Security/Safety, Guest Services

1 Bedroom8 Guests
New to Booking
$806
Average price / night
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St Pete Treat - 10 mins to beaches and downtown
St Pete Treat - 10 mins to beaches and downtown
House
St Petersburg, FL, USA
1.3k from Crossroads Area center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms6 Guests
9.7

Exceptional

6 reviews

$152
Average price / night
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Tiki it Easy - Luxury Home Minutes to Beach!
Tiki it Easy - Luxury Home Minutes to Beach!
House
St. Petersburg, FL, 33710, United States
1.5k from Crossroads Area center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$389
Average price / night
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Studio Apartment 5 minutes from beach
Studio Apartment 5 minutes from beach
Apartment
St. Petersburg, FL, USA
1.4k from Crossroads Area center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom4 Guests
9.4

Superb

14 reviews

$148
Average price / night
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Retro St Pete Home w/ Private Heated Pool
Retro St Pete Home w/ Private Heated Pool
House
St. Petersburg, FL, 33710-4429, United States
1.5k from Crossroads Area center

AC, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Kitchen, Laundry

3 Bedrooms7 Guests
9.0

Fabulous

2 reviews

$329
Average price / night
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King Size Sassy Studio
King Size Sassy Studio
House
St Petersburg, FL, USA
1.4k from Crossroads Area center

Oceanfront, Fireplace/Heating, Air Conditioner, Laundry, Smoking, Ocean View, Guest Services

1 Bedroom3 Guests
8.7

Fabulous

209 reviews

$100
Average price / night
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Centrally Located -  City of St. Petersburg, The Sun & Sand are Waiting for You
Centrally Located - City of St. Petersburg, The Sun & Sand are Waiting for You
Apartment
St. Petersburg, FL, 33710, United States
1.9k from Crossroads Area center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
9.4

Superb

117 reviews

$107
Average price / night
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Wave Cave - Beach, Heated Pool, BBQ, Family, Friends, Fun
Wave Cave - Beach, Heated Pool, BBQ, Family, Friends, Fun
House
Crossroads Area, St. Petersburg, Florida, USA
1.4k from Crossroads Area center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

3 Bedrooms10 Guests
9.7

Exceptional

3 reviews

$302
Average price / night
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Close to the beach! Gulfport 2BD/1BA King Bed Oasis, close to it all in St Pete
Close to the beach! Gulfport 2BD/1BA King Bed Oasis, close to it all in St Pete
House
St. Petersburg, FL, 33707, United States
1.9k from Crossroads Area center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

9 reviews

$255
Average price / night
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Retro St Pete Home with Private Heated Pool
Retro St Pete Home with Private Heated Pool
House
St Petersburg, FL, USA
1.5k from Crossroads Area center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

3 Bedrooms7 Guests
New to Booking
$237
Average price / night
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Stylish & Eclectic Modern 2/1 Apt – WeAreAuthentic
Stylish & Eclectic Modern 2/1 Apt – WeAreAuthentic
Apartment
South Pasadena, FL, 33707, United States
2.0k from Crossroads Area center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

39 reviews

$233
Average price / night
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Serene St Petersburg Home with Private Hot Tub
Serene St Petersburg Home with Private Hot Tub
House
St Petersburg, FL, USA
1.7k from Crossroads Area center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

3 Bedrooms8 Guests
New to Booking
$286
Average price / night
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Stylish & Eclectic Modern 2/2 Apt - WeAreGrateful
Stylish & Eclectic Modern 2/2 Apt - WeAreGrateful
Apartment
South Pasadena, FL, 33707, United States
2.1k from Crossroads Area center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
10.0

Exceptional

35 reviews

$237
Average price / night
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Vibrant Home with Pool Less Than 3 Mi to St Pete Beach
Vibrant Home with Pool Less Than 3 Mi to St Pete Beach
House
St Petersburg, FL, USA
2.0k from Crossroads Area center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$230
Average price / night
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Stylish & Eclectic Modern 2/2 Apt - WeArePeaceful
Stylish & Eclectic Modern 2/2 Apt - WeArePeaceful
Apartment
South Pasadena, FL, 33707, United States
2.1k from Crossroads Area center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
10.0

Exceptional

21 reviews

$238
Average price / night
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Private Solar heated salt water Pool- Minutes from everything in St. Pete!
Private Solar heated salt water Pool- Minutes from everything in St. Pete!
House
St. Petersburg, FL, 33710, United States
2.2k from Crossroads Area center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms7 Guests
10.0

Exceptional

31 reviews

$366
Average price / night
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Your Perfect Winter Getaway! 3br, 2ba with POOL
Your Perfect Winter Getaway! 3br, 2ba with POOL
House
St. Petersburg, FL, 33710, United States
2.2k from Crossroads Area center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$259
Average price / night
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3BR Family Home: SwimSpa, Huge Backyard, Volleyball Court, Fun Games
3BR Family Home: SwimSpa, Huge Backyard, Volleyball Court, Fun Games
House
South Pasadena, FL, 33707, United States
2.5k from Crossroads Area center

AC, Crib, Dryer, Heater, Hot Tub, Internet, Laundry, No Smoking, Patio

3 Bedrooms8 Guests
8.0

Good

2 reviews

$399
Average price / night
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Private Pool with waterfall and swim up bar at The Palm by DNY Prime
Private Pool with waterfall and swim up bar at The Palm by DNY Prime
House
St. Petersburg, FL, 33709, United States
2.5k from Crossroads Area center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$492
Average price / night
Check Availability
WATERFRONT w/ Rare Open Water Views + Private Pool
WATERFRONT w/ Rare Open Water Views + Private Pool
House
St. Petersburg, FL, 33710, United States
2.5k from Crossroads Area center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
9.2

Superb

35 reviews

$754
Average price / night
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PINK Coastal Pet-Friendly Home with Private Pool
PINK Coastal Pet-Friendly Home with Private Pool
House
Gulfport, FL, 33707, United States
2.5k from Crossroads Area center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
New to Booking
$337
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Crossroads Area.

Stay Near Crossroads Area's Top Attractions

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Crossroads Area Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2026 verified family-friendly vacation rentals in Crossroads Area. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Crossroads Area vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $66 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Crossroads Area offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Crossroads Area are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Crossroads Area often include amenities such as Child Friendly, View, and Fireplace/Heating. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.