Beach Home Rentals in Tropical Bay Estates, FL: Compare 10+ Sites & Save

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  4.  Florida

  5.  Big Pine Key
  6.  Tropical Bay Estates

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39 Beach Home Rentals in Tropical Bay Estates (Starting from $154)

Old Wooden Bridge Resort & Marina
Old Wooden Bridge Resort & Marina
Cabin
Big Pine Key, FL, USA
1.0k from Tropical Bay Estates center

Accommodations, Pools, Parking, Lodges, Cabins, Pet-friendly, Lodgings, Places to stay

43 Bedrooms138 Guests
8.4

Very Good

241 reviews

$257
Average price / night
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SEA EVERYWHERE!  Open Water & 2 Boat Basins!
SEA EVERYWHERE! Open Water & 2 Boat Basins!
House
Big Pine Key, FL, 33043, United States
0.1k from Tropical Bay Estates center

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

4 Bedrooms9 Guests
New to Booking
$462
Average price / night
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Magnolia's By The Sea
Magnolia's By The Sea
House
Big Pine Key, FL, USA
2.2k from Tropical Bay Estates center

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

2 Bedrooms11 Guests
New to Booking
$474
Average price / night
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SEA FOREVER! Gorgeous Ocean-Front Paradise!
SEA FOREVER! Gorgeous Ocean-Front Paradise!
House
Big Pine Key, FL, 33043, United States
0.1k from Tropical Bay Estates center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Internet, Kitchen

5 Bedrooms12 Guests
New to Booking
$574
Average price / night
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New listing 3bd/2bt Sleeps 8 \"Sunset Paradise Villa\" on canal Big Pine Key
New listing 3bd/2bt Sleeps 8 \"Sunset Paradise Villa\" on canal Big Pine Key
House
Big Pine Key, FL, 33043, United States
0.2k from Tropical Bay Estates center

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

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$246
Average price / night
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Sunrise Oasis in big pine key
Sunrise Oasis in big pine key
House
Big Pine Key, FL, 33043, United States
0.3k from Tropical Bay Estates center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$516
Average price / night
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A Serene Florida Escape in Big Pine Key 3 bed 2 bath house, pool, dock, sleep 8
A Serene Florida Escape in Big Pine Key 3 bed 2 bath house, pool, dock, sleep 8
House
Big Pine Key, FL, 33043, United States
0.3k from Tropical Bay Estates center

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

3 Bedrooms8 Guests
New to Booking
$410
Average price / night
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Private water front property with ocean access
Private water front property with ocean access
House
Big Pine Key, FL, 33043, United States
0.7k from Tropical Bay Estates center

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

3 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$555
Average price / night
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Tropical Canal-front Cottage in the Lower Florida Keys
Tropical Canal-front Cottage in the Lower Florida Keys
House
Big Pine Key, FL, 33043, United States
0.8k from Tropical Bay Estates center

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

2 Bedrooms8 Guests
New to Booking
$229
Average price / night
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Old Wooden Bridge Resort and Marina
Old Wooden Bridge Resort and Marina
Cottage
1791 Bogie Drive, Big Pine Key, FL, 33043, United States
1.0k from Tropical Bay Estates center

AC, Barbecue, Free Parking, Heater, Internet, Living Area, Microwave, Outdoor Space, Pool

1 Bedroom4 Guests
8.6

Fabulous

316 reviews

$311
Average price / night
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POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
House
Big Pine Key, FL, 33043, United States
1.0k from Tropical Bay Estates center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$451
Average price / night
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Honey Hole a Big Pine Key paradise, canal to Bogie Channel
Honey Hole a Big Pine Key paradise, canal to Bogie Channel
House
Big Pine Key, FL, 33043, United States
1.1k from Tropical Bay Estates center

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

2 Bedrooms8 Guests
New to Booking
$349
Average price / night
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3-bedroom waterfront. Cable, WiFi, AC, Hot tub, Dock. Spring 2026 Available !!
3-bedroom waterfront. Cable, WiFi, AC, Hot tub, Dock. Spring 2026 Available !!
House
Big Pine Key, FL, 33043, United States
1.1k from Tropical Bay Estates center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$351
Average price / night
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SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT
House
Big Pine Key, FL, 33043, United States
1.1k from Tropical Bay Estates center

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

2 Bedrooms6 Guests
10.0

Exceptional

23 reviews

$258
Average price / night
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Escape the Ordinary and Experience Island Paradise
Escape the Ordinary and Experience Island Paradise
House
Big Pine Key, FL, 33043, United States
1.1k from Tropical Bay Estates center

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

2 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$241
Average price / night
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Secluded Tropical Retreat: 60' Dock, Large Pool, World-Class Fishing & Lobster
Secluded Tropical Retreat: 60' Dock, Large Pool, World-Class Fishing & Lobster
House
Big Pine Key, FL, 33043, United States
1.2k from Tropical Bay Estates center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$416
Average price / night
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Oceanfront Paradise w new 365' Dock Huge Tiki and Firepit.  Dogs OK
Oceanfront Paradise w new 365' Dock Huge Tiki and Firepit. Dogs OK
House
Big Pine Key, FL, 33043, United States
1.2k from Tropical Bay Estates center

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

3 Bedrooms6 Guests
9.4

Superb

20 reviews

$463
Average price / night
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Incredible~Ocean Views~ramp-dock-hot tub. Stay 14 days get up to 14 more FREE!
Incredible~Ocean Views~ramp-dock-hot tub. Stay 14 days get up to 14 more FREE!
House
Big Pine Key, FL, 33043, United States
1.3k from Tropical Bay Estates center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$513
Average price / night
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Mickey and Lynn's House of Windows
Mickey and Lynn's House of Windows
House
Big Pine Key, FL, 33050, United States
1.7k from Tropical Bay Estates center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms7 Guests
10.0

Exceptional

8 reviews

$403
Average price / night
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Canal Front Home in Big Pine Key with Pool
Canal Front Home in Big Pine Key with Pool
House
BIG PINE KEY, FL, 33043, United States
1.7k from Tropical Bay Estates center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$283
Average price / night
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9 Mi to Bahia Honda State Park: Big Pine Key Oasis
9 Mi to Bahia Honda State Park: Big Pine Key Oasis
House
Big Pine Key, FL, 33043, United States
1.9k from Tropical Bay Estates center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$154
Average price / night
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Paradise Retreat ~ BPK
Paradise Retreat ~ BPK
House
Big Pine Key, FL, 33043, United States
1.9k from Tropical Bay Estates center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$216
Average price / night
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Waterfront Pool Home! - Heavenly Hideout - Big Pine Key
Waterfront Pool Home! - Heavenly Hideout - Big Pine Key
House
Big Pine Key, FL, 33043, United States
1.9k from Tropical Bay Estates center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$229
Average price / night
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Open 360 water view,  boat dockage, 4 bedroom Home in Big Pine Key
Open 360 water view, boat dockage, 4 bedroom Home in Big Pine Key
House
Big Pine Key, FL, 33043, United States
2.0k from Tropical Bay Estates center

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

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$623
Average price / night
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Frigate Landing - Beautiful Waterfront home,60ft seawall,Tiki Hut, Pet Friendly,
Frigate Landing - Beautiful Waterfront home,60ft seawall,Tiki Hut, Pet Friendly,
House
Big Pine Key, FL, 33043, United States
2.2k from Tropical Bay Estates center

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

3 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$193
Average price / night
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Lower Keys Retreat.....  Come....  Relax in Paradise!!
Lower Keys Retreat..... Come.... Relax in Paradise!!
House
Big Pine Key, FL, 33043, United States
2.2k from Tropical Bay Estates center

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

3 Bedrooms8 Guests
9.8

Exceptional

17 reviews

$337
Average price / night
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Waterfront Home in The Fabulous Florida Keys with Peak-A-Boo Views of the Bay!
Waterfront Home in The Fabulous Florida Keys with Peak-A-Boo Views of the Bay!
House
Big Pine Key, FL, 33043, United States
2.2k from Tropical Bay Estates center

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

2 Bedrooms6 Guests
9.6

Exceptional

14 reviews

$209
Average price / night
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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 Beach Rentals in Tropical Bay Estates.

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Frequently Asked Questions

You can explore 39 verified beach rentals in Tropical Bay Estates. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Tropical Bay Estates vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $154 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Tropical Bay Estates offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Tropical Bay Estates welcome pets. Currently, 25 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Tropical Bay Estates often include amenities designed for coastal living, such as View, Ocean View, and Balcony/Terrace. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.