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

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Big Pine Key
  6.  Tropical Bay Estates

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92 Best Oceanfront 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 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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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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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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Parmer's Resort
Parmer's Resort
Resort
Little Torch Key, FL, USA
3.9k from Tropical Bay Estates center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, Lodgings, Beach, Places to stay

29 Bedrooms37 Guests
8.6

Fabulous

440 reviews

$215
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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Experience Coastal Living at its Best Florida Keys
Experience Coastal Living at its Best Florida Keys
House
Summerland Key, FL, USA
6.2k from Tropical Bay Estates center

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

1 Bedroom4 Guests
New to Booking
$293
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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Ocean Depth Room at Barnacle Resort
Ocean Depth Room at Barnacle Resort
Apartment
Big Pine Key, FL, USA
6.6k from Tropical Bay Estates center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay

1 Bedroom4 Guests
7.3

Good

3 reviews

$505
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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Ocean View Room at Barnacle Resort
Ocean View Room at Barnacle Resort
Apartment
Big Pine Key, FL, USA
6.6k from Tropical Bay Estates center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay, Family

1 Bedroom4 Guests
9.5

Superb

4 reviews

$492
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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Star Room at Barnacle Resort
Star Room at Barnacle Resort
Apartment
Big Pine Key, FL, USA
6.6k from Tropical Bay Estates center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay, Family

1 Bedroom2 Guests
9.0

Fabulous

2 reviews

$385
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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Beach View Room at Barnacle Resort
Beach View Room at Barnacle Resort
Apartment
Big Pine Key, FL, USA
6.6k from Tropical Bay Estates center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay

1 Bedroom2 Guests
New to Booking
$499
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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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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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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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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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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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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Big Pine Getaway - Pets + Boats Welcome
Big Pine Getaway - Pets + Boats Welcome
House
Big Pine Key, FL, 33043, United States
2.4k from Tropical Bay Estates center

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

4 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$251
Average price / night
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Charming 2-bedroom 2- bath home located in the middle of The Key Deer Refuge.
Charming 2-bedroom 2- bath home located in the middle of The Key Deer Refuge.
House
Big Pine Key, FL, 33043, United States
2.5k from Tropical Bay Estates center

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

2 Bedrooms4 Guests
10.0

Exceptional

8 reviews

$322
Average price / night
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Peaceful Big Pine Tropical Seaside-BP#22
Peaceful Big Pine Tropical Seaside-BP#22
House
Big Pine Key, FL, 33043, United States
2.6k from Tropical Bay Estates center

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

3 Bedrooms8 Guests
New to Booking
$274
Average price / night
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Captain & Mermaid's Diamond #BP25
Captain & Mermaid's Diamond #BP25
House
Big Pine Key, FL, 33043, United States
2.6k from Tropical Bay Estates center

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

1 Bedroom4 Guests
New to Booking
$196
Average price / night
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Boaters Paradise on a Deep Canal
Boaters Paradise on a Deep Canal
House
Big Pine Key, FL, 33043, United States
2.6k from Tropical Bay Estates center

AC, Balcony, Dryer, Heater, Internet, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
New to Booking
$294
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 Oceanfront Rentals in Tropical Bay Estates.

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Frequently Asked Questions

You can explore 92 verified oceanfront rentals in Tropical Bay Estates. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Tropical Bay Estates vary depending on the property size, exact beachfront location, and season. Rates typically start from around $154 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Tropical Bay Estates offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Tropical Bay Estates welcome pets. Currently, 35 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Tropical Bay Estates often include features designed for a comfortable coastal stay, such as View, Ocean View, and Oceanfront. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.