Owner Direct Cottages in Summerland Key

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45 Summerland Key Cottage Rentals From $248

Looking for a quiet cottage stay in Summerland Key? Uncover a curated selection of quaint countryside properties and seaside escapes offering comfort and local charm. Compare verified listings to plan your next peaceful getaway.

 Starfish Cottage - Summer fun.  Sleeps 4 -boating fishing and Lobster 🦞 season.
Starfish Cottage - Summer fun. Sleeps 4 -boating fishing and Lobster 🦞 season.
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

62 reviews

$305
Average price / night
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Ocean Breeze House - Summer fun Sleeps 8 boating, fishing and 🦞 Lobster season.
Ocean Breeze House - Summer fun Sleeps 8 boating, fishing and 🦞 Lobster season.
Cottage
Summerland Key, FL, 33042, United States
0.8k from Summerland Key center

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

2 Bedrooms8 Guests
9.4

Superb

32 reviews

$541
Average price / night
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PALM COTTAGE - Sleeps 4  summer fun ..lobster season.
PALM COTTAGE - Sleeps 4 summer fun ..lobster season.
Cottage
Summerland Key, FL, 33042, United States
1.1k from Summerland Key center

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

1 Bedroom4 Guests
9.8

Exceptional

55 reviews

$329
Average price / night
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FLAMINGO COTTAGE summer fun. Pool, boating, fishing lobster season.
FLAMINGO COTTAGE summer fun. Pool, boating, fishing lobster season.
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

$301
Average price / night
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SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster
SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster
Cottage
Summerland Key, FL, 33042, United States
1.2k from Summerland Key center

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

1 Bedroom2 Guests
9.6

Exceptional

44 reviews

$248
Average price / night
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Peaceful ocean front cottage.
Peaceful ocean front cottage.
Cottage
Summerland Key, FL, 33042, United States
1.6k from Summerland Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$379
Average price / night
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**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Cottage
Cudjoe Key, FL, 33042, United States
2.5k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

218 reviews

$467
Average price / night
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**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Cottage
Cudjoe Key, FL, 33042, United States
2.5k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

50 reviews

$482
Average price / night
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Sea Breeze Cottage - Venture Out Unit 066
Sea Breeze Cottage - Venture Out Unit 066
Cottage
Cudjoe Key, FL, 33042, United States
2.5k from Summerland Key center

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

2 Bedrooms4 Guests
8.0

Good

17 reviews

$403
Average price / night
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Beautiful Cottage & Amenities in Gated Community
Beautiful Cottage & Amenities in Gated Community
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$422
Average price / night
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Canal front with open water views in Venture Out - Lot 529
Canal front with open water views in Venture Out - Lot 529
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$419
Average price / night
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35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
Cottage
CUDJOE KEY, FL, 33042, United States
2.6k from Summerland Key center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
9.8

Exceptional

132 reviews

$393
Average price / night
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OCEANIA... water front cottage retreat ~
OCEANIA... water front cottage retreat ~
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

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

2 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$1222
Average price / night
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Mile Marker Mahi - Venture Out #465
Mile Marker Mahi - Venture Out #465
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.6

Exceptional

55 reviews

$423
Average price / night
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FL Keys Cottage with Ocean Views - Venture Out Unit 395
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
8.4

Very Good

8 reviews

$354
Average price / night
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Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Summerland Key center

AC, Balcony, Barbecue, Heater, Hot Tub, Internet, Kitchen, Living Area, Microwave

2 Bedrooms6 Guests
9.6

Exceptional

14 reviews

$689
Average price / night
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Cozy, Perfect Conch Cottage! - VO315
Cozy, Perfect Conch Cottage! - VO315
Cottage
Summerland Key, FL, 33042, United States
2.7k from Summerland Key center

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

2 Bedrooms4 Guests
9.2

Superb

33 reviews

$360
Average price / night
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2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cottage
Cudjoe Key, FL, 33042, United States
2.7k from Summerland Key center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
9.8

Exceptional

31 reviews

$707
Average price / night
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Breezy Point - Venture Out Unit 199
Breezy Point - Venture Out Unit 199
Cottage
Cudjoe Key, FL, 33042, United States
2.8k from Summerland Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
New to Booking
$300
Average price / night
Check Availability
Waterfront Home
Waterfront Home
Cottage
Cudjoe Key, FL, 33042, United States
2.8k from Summerland Key center

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

2 Bedrooms4 Guests
8.8

Fabulous

187 reviews

$455
Average price / night
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A slice of paradise
A slice of paradise
Cottage
Cudjoe Key, FL, 33042, United States
2.8k from Summerland Key center

AC, Arcade, Barbecue, Crib, Free Parking, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.0

Fabulous

100 reviews

$324
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental 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 Cottage Rentals in Summerland Key.

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Frequently Asked Questions

There are a lot of options in Summerland Key. If you plan on staying in the Summerland Key area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Summerland Key

You can explore 45 verified cottage rentals in Summerland Key. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Summerland Key vary based on the season, location, and amenities offered. Rates typically start from around $248 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Summerland Key feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 22 listings in Summerland Key welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it's a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Summerland Key are known for their comfort and charm, often including amenities such as Kitchen, Bedding/Linens, and Laundry. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Summerland Key are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.