Oceanfront Rentals in Summerland Key, FL: Compare 10+ Sites & Save

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233 Best Oceanfront Rentals in Summerland Key (Starting from $242)

Turtle Cove Views by Last Key Realty
Turtle Cove Views by Last Key Realty
House
Cudjoe Key, FL, USA
2.5k from Summerland Key center

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

2 Bedrooms6 Guests
7.0

Good

1 reviews

$513
Average price / night
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Summerland Serenity  Elevated Waterfront Luxury with Private Elevator & Pool
Summerland Serenity Elevated Waterfront Luxury with Private Elevator & Pool
House
Summerland Key, FL, 33042, United States
0.4k from Summerland Key center

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

5 Bedrooms12 Guests
New to Booking
$508
Average price / night
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Island Oasis ~ YOUR Paradise Awaits!
Island Oasis ~ YOUR Paradise Awaits!
House
Summerland Key, Florida, USA
2.5k from Summerland Key center

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

2 Bedrooms6 Guests
7.4

Good

5 reviews

$386
Average price / night
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Mariners Cove - The Kraken House
Mariners Cove - The Kraken House
House
Summerland Key, FL, 33042, United States
0.6k from Summerland Key center

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

5 Bedrooms10 Guests
9.8

Exceptional

9 reviews

$698
Average price / night
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OCEANIA. water front cottage retreat ~
OCEANIA. water front cottage retreat ~
Villa
Cudjoe Key, FL, USA
2.6k from Summerland Key center

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

2 Bedrooms6 Guests
9.4

Superb

16 reviews

$826
Average price / night
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 Starfish Cottage - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
Starfish Cottage - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
Cottage
Summerland Key, FL, 33042, United States
0.8k from Summerland Key center

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

1 Bedroom4 Guests
9.8

Exceptional

60 reviews

$243
Average price / night
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NAUTILUS.ocean front cottage retreat ~
NAUTILUS.ocean front cottage retreat ~
Villa
Cudjoe Key, FL, USA
2.6k from Summerland Key center

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

2 Bedrooms6 Guests
9.2

Superb

16 reviews

$908
Average price / night
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Amazing 2 BR Home in Summerland w/ Great Boating Access & Private Heated Pool!
Amazing 2 BR Home in Summerland w/ Great Boating Access & Private Heated Pool!
House
Summerland Key, FL, 33042, United States
1.0k from Summerland Key center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$367
Average price / night
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Pelican's Roost, Waterfront comfort at Venture Out
Pelican's Roost, Waterfront comfort at Venture Out
House
Cudjoe Key, FL, USA
2.7k from Summerland Key center

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

2 Bedrooms5 Guests
9.2

Superb

15 reviews

$303
Average price / night
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Beautiful Oceanfront Villa with Pool and near Key West, Florida
Beautiful Oceanfront Villa with Pool and near Key West, Florida
Villa
Summerland Key, FL, 33042, United States
1.1k from Summerland Key center

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

2 Bedrooms5 Guests
New to Booking
$621
Average price / night
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Dolphin Daydreams by Last Key Realty
Dolphin Daydreams by Last Key Realty
House
Cudjoe Key, FL, USA
2.7k from Summerland Key center

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

1 Bedroom4 Guests
New to Booking
$351
Average price / night
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REEL ESCAPE - 4 Bedroom / 2 Bathroom w/ Pool, Boat Dock & Sleeps 8!
REEL ESCAPE - 4 Bedroom / 2 Bathroom w/ Pool, Boat Dock & Sleeps 8!
House
Summerland Key, FL, 33042, United States
1.1k from Summerland Key center

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

4 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$544
Average price / night
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Serenity Now Seaside Escape - Brand New Build!
Serenity Now Seaside Escape - Brand New Build!
House
Cudjoe Key, FL, USA
2.8k from Summerland Key center

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

1 Bedroom6 Guests
New to Booking
$469
Average price / night
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FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
Cottage
Summerland Key, FL, 33042, United States
1.1k from Summerland Key center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, Outdoor Grill

1 Bedroom4 Guests
9.8

Exceptional

47 reviews

$242
Average price / night
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Oceanview Retreat with 60ft Seawall
Oceanview Retreat with 60ft Seawall
House
Cudjoe Key, FL, USA
2.8k from Summerland Key center

Ocean View, Hot Tub, Pool, Barbecue/Outdoor Cooking, Security/Safety, Air Conditioner, Balcony/Terrace

2 Bedrooms4 Guests
New to Booking
$608
Average price / night
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PEACEFUL PARADISE DEEP WATER CANAL! MINUTES TO OCEAN \nFishing and Lobster season
PEACEFUL PARADISE DEEP WATER CANAL! MINUTES TO OCEAN \nFishing and Lobster season
House
Summerland Key, FL, 33042, United States
1.3k from Summerland Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$480
Average price / night
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Parrotfish Pointe
Parrotfish Pointe
House
Cudjoe Key, FL, USA
3.7k from Summerland Key center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

3 Bedrooms6 Guests
New to Booking
$301
Average price / night
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Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
House
Summerland Key, FL, 33042, United States
1.3k from Summerland Key center

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

3 Bedrooms8 Guests
9.6

Exceptional

58 reviews

$319
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
4.4k from Summerland Key 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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3/2 on the Water in Paradise Monthly Rental 28 Day min.
3/2 on the Water in Paradise Monthly Rental 28 Day min.
House
Summerland Key, FL, 33042, United States
1.5k from Summerland Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$289
Average price / night
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Ocean View with Pool, 4 bedroom Vila Near Key West
Ocean View with Pool, 4 bedroom Vila Near Key West
Villa
Cudjoe Key, FL, USA
5.3k from Summerland Key center

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

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$810
Average price / night
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One of the very few beach houses with a daily, rental license in the Keys.
One of the very few beach houses with a daily, rental license in the Keys.
House
Summerland Key, FL, 33042, United States
1.5k from Summerland Key center

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

4 Bedrooms12 Guests
8.8

Fabulous

67 reviews

$1296
Average price / night
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Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West
Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West
House
Summerland Key, FL, 33042, United States
1.7k from Summerland Key center

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

5 Bedrooms14 Guests
New to Booking
$536
Average price / night
Check Availability
Fishermens' dream B.Y.O. boat ocean front with protected canal 600' to bluewater
Fishermens' dream B.Y.O. boat ocean front with protected canal 600' to bluewater
House
Summerland Key, FL, 33042, United States
2.2k from Summerland Key center

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

2 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$349
Average price / night
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Casa Kiwi #472 - Ocean Views on Cudjoe Key
Casa Kiwi #472 - Ocean Views on Cudjoe Key
House
Cudjoe Key, FL, 33042, United States
2.5k from Summerland Key center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$347
Average price / night
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Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
House
Cudjoe Key, FL, 33042, United States
2.5k from Summerland Key center

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

2 Bedrooms4 Guests
9.8

Exceptional

17 reviews

$943
Average price / night
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ARTIST HOUSE ~ Canal Front 4 BR/3.5 Ba Home w/ Pool & Ocean and Gulf Access!
ARTIST HOUSE ~ Canal Front 4 BR/3.5 Ba Home w/ Pool & Ocean and Gulf Access!
House
Cudjoe Key, FL, 33042, United States
2.5k from Summerland Key center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$414
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 Summerland Key.

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Summerland Key Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 233 verified oceanfront rentals in Summerland Key. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Summerland Key vary depending on the property size, exact beachfront location, and season. Rates typically start from around $242 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 Summerland Key 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 Summerland Key welcome pets. Currently, 28 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 Summerland Key often include features designed for a comfortable coastal stay, such as Ocean View, Oceanfront, and View. 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.