Oceanfront Rentals in Saint Mary Star of the Sea, FL: Compare 10+ Sites & Save

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1053 Best Oceanfront Rentals in Saint Mary Star of the Sea (Starting from $225)

Elizabeth's Secret - Old Town Key West
Elizabeth's Secret - Old Town Key West
House
Key West, FL, USA
0.2k from Saint Mary Star of the Sea center

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

3 Bedrooms6 Guests
New to Booking
$1628
Average price / night
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**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.0k from Saint Mary Star of the Sea center

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

5 Bedrooms12 Guests
10.0

Exceptional

141 reviews

$2193
Average price / night
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Courtney's Place Historic Cottages & Inns
Courtney's Place Historic Cottages & Inns
House
Saint Mary Star of the Sea, Key West, Florida, USA
0.4k from Saint Mary Star of the Sea center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Romantic, Pet-friendly, Lodgings

18 Bedrooms72 Guests
8.8

Fabulous

1291 reviews

$738
Average price / night
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CASA DEL SUR ~ Renovated 2 BR/2Ba Home with Heated Dip Pool!
CASA DEL SUR ~ Renovated 2 BR/2Ba Home with Heated Dip Pool!
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

2 Bedrooms4 Guests
New to Booking
$382
Average price / night
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H2O Suites- Adults Only
H2O Suites- Adults Only
Resort
Saint Mary Star of the Sea, Key West, Florida, USA
0.5k from Saint Mary Star of the Sea center

Luxury, Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Places to stay

22 Bedrooms6 Guests
9.5

Superb

508 reviews

$1688
Average price / night
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**THE SOPHISTICATED SANDPIPER @ OLD TOWN** Home & Pool Near Duval + LAST KEY SER
**THE SOPHISTICATED SANDPIPER @ OLD TOWN** Home & Pool Near Duval + LAST KEY SER
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

3 Bedrooms6 Guests
New to Booking
$1233
Average price / night
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Key West Villas
Key West Villas
Villa
Key West, FL, USA
0.5k from Saint Mary Star of the Sea center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

9 Bedrooms28 Guests
9.7

Exceptional

379 reviews

$345
Average price / night
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**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

3 Bedrooms8 Guests
9.8

Exceptional

135 reviews

$1181
Average price / night
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Alexander Palms Court - No Hidden Resort Fees!
Alexander Palms Court - No Hidden Resort Fees!
House
Key West, FL, USA
0.5k from Saint Mary Star of the Sea center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

12 Bedrooms35 Guests
8.6

Fabulous

894 reviews

$225
Average price / night
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**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

8 Bedrooms16 Guests
10.0

Exceptional

51 reviews

$2380
Average price / night
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New Orleans House - Gay Male Adult Guesthouse
New Orleans House - Gay Male Adult Guesthouse
House
Saint Mary Star of the Sea, Key West, Florida, USA
0.5k from Saint Mary Star of the Sea center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Hot tubs

13 Bedrooms28 Guests
8.8

Fabulous

193 reviews

$575
Average price / night
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**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

4 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$431
Average price / night
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Heron Hideaway
Heron Hideaway
Apartment
Key West, FL, USA
0.6k from Saint Mary Star of the Sea center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Family

1 Bedroom4 Guests
9.3

Superb

6 reviews

$384
Average price / night
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**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

3 Bedrooms8 Guests
10.0

Exceptional

87 reviews

$1199
Average price / night
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Santa Maria Suites Resort
Santa Maria Suites Resort
Resort
Key West, FL, USA
0.6k from Saint Mary Star of the Sea center

Accommodations, Pools, Resorts, Parking, Romantic, Boutique, 4-star, Lodgings, Places to stay

35 Bedrooms20 Guests
9.3

Superb

674 reviews

$432
Average price / night
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Tropical Tranquility - 4BR Luxury Villa In Old Town Key West  w Pool
Tropical Tranquility - 4BR Luxury Villa In Old Town Key West w Pool
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

4 Bedrooms8 Guests
10.0

Exceptional

59 reviews

$1596
Average price / night
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The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton
Resort
Key West, FL, USA
0.7k from Saint Mary Star of the Sea center

Accommodations, Pools, Resorts, Parking, Spa, Pet-friendly, 4-star, Lodgings, Beach

130 Bedrooms42 Guests
7.6

Good

287 reviews

$418
Average price / night
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WINDSONG DELIGHT - Cute house on Windsor Ln
WINDSONG DELIGHT - Cute house on Windsor Ln
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

AC, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Patio

2 Bedrooms4 Guests
New to Booking
$267
Average price / night
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Tranquillity Guest House
Tranquillity Guest House
Apartment
Key West, FL, USA
0.8k from Saint Mary Star of the Sea center

Apartments, Cheap, Accommodations, Pools, Serviced apartments, 3-star, Lodgings, Places to stay

16 Bedrooms4 Guests
8.2

Very Good

255 reviews

$514
Average price / night
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Monkey House by AvantStay | Pool, by Duval Street
Monkey House by AvantStay | Pool, by Duval Street
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

2 Bedrooms4 Guests
New to Booking
$292
Average price / night
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~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!
~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!
Cottage
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1024
Average price / night
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~ROYAL POINCIANA COTTAGE~ Come and indulge yourself in some KW sunshine!
~ROYAL POINCIANA COTTAGE~ Come and indulge yourself in some KW sunshine!
Cottage
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

AC, Barbecue, Dryer, Internet, Laundry, Microwave, No Smoking, Patio, Pool

1 Bedroom2 Guests
8.0

Good

6 reviews

$420
Average price / night
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~MARGARITA COTTAGE~ Bask in sunshine and lounge by your pool in paradise.
~MARGARITA COTTAGE~ Bask in sunshine and lounge by your pool in paradise.
Cottage
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

AC, Barbecue, Dryer, Internet, Laundry, Microwave, No Smoking, Patio, Pool

1 Bedroom2 Guests
9.8

Exceptional

7 reviews

$436
Average price / night
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Passover Cottage | Private Pool & Ideal Key West Location
Passover Cottage | Private Pool & Ideal Key West Location
House
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

AC, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Grill, Patio

2 Bedrooms4 Guests
10.0

Exceptional

13 reviews

$1001
Average price / night
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DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
House
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

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

4 Bedrooms8 Guests
9.8

Exceptional

18 reviews

$1736
Average price / night
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**WINDWARD WAVES @ OLD TOWN** Cozy Cottage Near Duval + LAST KEY SERVICES...
**WINDWARD WAVES @ OLD TOWN** Cozy Cottage Near Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

4 Bedrooms6 Guests
New to Booking
$668
Average price / night
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**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

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

6 Bedrooms12 Guests
10.0

Exceptional

14 reviews

$524
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 Oceanfront Rentals in Saint Mary Star of the Sea.

Where to stay in Saint Mary Star of the Sea? Best neighborhoods & areas

Saint Mary Star of the Sea Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 1053 verified oceanfront rentals in Saint Mary Star of the Sea. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Saint Mary Star of the Sea vary depending on the property size, exact beachfront location, and season. Rates typically start from around $225 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 Saint Mary Star of the Sea 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 Saint Mary Star of the Sea welcome pets. Currently, 38 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 Saint Mary Star of the Sea 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.