Vacation rentals in Summerland Key - HomeToGo base64Hash Vacation rentals in Summerland Key - HomeToGo

Vacation rentals in Summerland Key

Browse 197 available vacation homes and compared across 9 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • House
    • Apartment
    • Private room

  • Distance to center

    • 2 mi
    • 3 mi
    • Any

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • Air conditioning
    • WiFi
    • Kitchen
    • TV
    • Washing machine
    • Parking
    • Balcony/patio
    • Microwave
    • Dishwasher
    • Yard
    • Hot tub
    • Fireplace
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Fishing
    • Grill

Top 15 most Recommended Vacation Rentals in Summerland Key

Discover your ideal Summerland Key vacation rental with real-time comparisons of 197 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Summerland Key
House ∙ 4 guests ∙ 2 bedrooms

House with barbecue, patio & jacuzzi

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a kitchen, fireplace, hot tub, and parking for a perfect getaway.
from $347
per night
Outstanding(17 ratings)
from $347
per night
View deal
House Summerland Key
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly vacation home with private pool, garden & patio | Good for workation

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private heated pool, balcony, and yard, perfect for family vacations.
from $608
per night
Outstanding(88 ratings)
from $608
per night
View deal
House Summerland Key
House ∙ 6 guests ∙ 2 bedrooms

House with patio, garden & barbecue | Nature view

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key offers beach access, a kitchen, balcony, yard, and parking for an unforgettable getaway.
from $384
per night
Outstanding(67 ratings)
from $384
per night
View deal
House Summerland Key
House ∙ 8 guests ∙ 3 bedrooms

Big vacation home with patio, private pool & barbecue

Summerland Key, Monroe County, Florida, United States
This waterfront house rental on Summerland Key features a private pool, a kitchen, and space for up to 8 guests.
from $326
per night
Outstanding(2 ratings)
from $326
per night
View deal
House Summerland Key
House ∙ 6 guests ∙ 2 bedrooms

Family-friendly beautiful vacation home with patio, jacuzzi & barbecue | Pets allowed

Summerland Key, Monroe County, Florida, United States
This waterfront house in Summerland Key features a hot tub, kitchen, beach access, and space for six, perfect for family getaways.
from $365
per night
Outstanding(20 ratings)
from $365
per night
View deal
House Summerland Key
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with grill, private pool & patio

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key features a private heated pool, a kitchen, and a balcony for up to 8 guests to enjoy.
from $355
per night
Outstanding(10 ratings)
from $355
per night
View deal
House Summerland Key
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with patio, BBQ & private pool

Summerland Key, Monroe County, Florida, United States
This Summerland Key house rental features a private heated pool, kitchen, and balcony, perfect for accommodating up to 10 guests.
from $935
per night
Outstanding(52 ratings)
from $935
per night
View deal
House Summerland Key
House ∙ 8 guests ∙ 3 bedrooms

House with barbeque, garden & patio

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private pool, beach access, and a yard, perfect for families and pets.
from $183
per night
Outstanding(65 ratings)
from $183
per night
View deal
House Summerland Key
House ∙ 8 guests ∙ 3 bedrooms

House with patio, barbecue & private pool

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private heated pool, a full kitchen, and a balcony for family fun.
from $391
per night
Outstanding(37 ratings)
from $391
per night
View deal
House Summerland Key
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped wonderful vacation home with private pool, patio & BBQ

Summerland Key, Monroe County, Florida, United States
from $512
per night
Excellent(14 ratings)
from $512
per night
View deal
House Summerland Key
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented pleasant house with terrace, grill & pool | Suitable for remote work

Summerland Key, Monroe County, Florida, United States
from $473
per night
Outstanding(4 ratings)
from $473
per night
View deal
House Summerland Key
House ∙ 7 guests ∙ 3 bedrooms

Vacation home with barbeque & terrace

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a balcony, kitchen, and parking, accommodating up to seven guests and pets.
from $186
per night
Outstanding(27 ratings)
from $186
per night
View deal
House Summerland Key
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, private pool & barbecue | Nature view

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private pool, yard, and kitchen, perfect for family getaways.
from $317
per night
Outstanding(5 ratings)
from $317
per night
View deal
House Summerland Key
House ∙ 10 guests ∙ 3 bedrooms

House with private pool, grill & terrace | Pets are welcome

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private pool, kitchen, and accommodates up to 10 guests with pets allowed.
from $205
per night
Very good(2 ratings)
from $205
per night
View deal
House Summerland Key
House ∙ 6 guests ∙ 3 bedrooms

House with private pool, terrace & BBQ | Suitable for remote work

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key offers a private heated pool, kitchen, balcony, and space for up to six guests.
from $235
per night
Outstanding(24 ratings)
from $235
per night
View deal

Vacation rentals and apartments with air conditioning

House Summerland Key
from $315
per night
House ∙ 6 guests ∙ 2 bedrooms

Family-oriented vacation home with private pool, grill & terrace | Nature view

5.0
Outstanding(6 ratings)
Summerland Key, Monroe County, Florida, United States
Air conditioning
View deal
House Summerland Key
from $486
per night
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly spacious vacation home with patio & barbecue | Good for workation | Pets allowed

4.9
Outstanding(27 ratings)
Summerland Key, Monroe County, Florida, United States
Air conditioning
View deal
Cabin Summerland Key
from $422
per night
Cabin ∙ 8 guests ∙ 2 bedrooms

Cottage with BBQ & pool

4.7
Excellent(52 ratings)
Summerland Key, Monroe County, Florida, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

House Summerland Key
from $360
per night
House ∙ 10 guests ∙ 4 bedrooms

Pleasant vacation home with terrace & private pool

Summerland Key, Monroe County, Florida, United States
Balcony
View deal
House Summerland Key
from $363
per night
House ∙ 6 guests ∙ 3 bedrooms

House with private pool, terrace & barbeque | Good for workation

5.0
Outstanding(2 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony
View deal
House Summerland Key
from $337
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with private pool, terrace & barbeque | Nature view | Perfect for remote work

5.0
Outstanding(21 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

House Summerland Key
from $214
per night
House ∙ 5 guests ∙ 2 bedrooms

Vacation home with terrace, barbeque & private pool

3.7
Good(18 ratings)
Summerland Key, Monroe County, Florida, United States
Fireplace
View deal
House Summerland Key
from $549
per night
House ∙ 7 guests ∙ 3 bedrooms

Fully equipped vacation home with patio, BBQ & private pool

4.3
Very good(4 ratings)
Summerland Key, Monroe County, Florida, United States
Fireplace
View deal
House Summerland Key
from $283
per night
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, barbecue & jacuzzi | Nature view

5.0
Outstanding(8 ratings)
Summerland Key, Monroe County, Florida, United States
Fireplace
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Summerland Key offering exceptional value for money

House Summerland Key
from $266
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented ample house with private pool, barbeque & terrace | Water view

5.0
Outstanding(6 ratings)
Summerland Key, Monroe County, Florida, United States
View deal
House Summerland Key
from $225
per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped lovely house with yard, barbecue & patio | Nature view | Pet-friendly

5.0
Outstanding(26 ratings)
Summerland Key, Monroe County, Florida, United States
View deal
House Summerland Key
from $294
per night
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped vacation home with grill | Pets are welcome

5.0
Outstanding(23 ratings)
Summerland Key, Monroe County, Florida, United States
View deal

Top-Rated Vacation rentals in Summerland Key

Book the highest-rated Summerland Key vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Summerland Key
from $170
per night
House ∙ 8 guests ∙ 3 bedrooms

House with garden, barbeque & terrace

5.0
Outstanding(21 ratings)
Summerland Key, Monroe County, Florida, United States
View deal
House Summerland Key
from $480
per night
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly lovely vacation home with grill, terrace & yard | Nature view | Suitable for remote work | Dogs allowed

5.0
Outstanding(6 ratings)
Summerland Key, Monroe County, Florida, United States
View deal
House Summerland Key
from $617
per night
House ∙ 7 guests ∙ 3 bedrooms

Family-friendly vacation home with terrace, jacuzzi & private pool | Perfect for remote work

5.0
Outstanding(4 ratings)
Summerland Key, Monroe County, Florida, United States
View deal

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Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities in Summerland Key

  • Pool (124)
  • Pet-friendly (102)
  • Air conditioning (191)
  • WiFi (189)
  • Kitchen (186)
  • TV (185)
  • Fishing (104)
  • Washing machine (151)
  • Parking (6)
  • Grill (142)
  • Balcony/patio (116)
  • Microwave (176)

Finding a property with a pool shouldn't be too difficult in Summerland Key. Many of the vacation rentals include pools. Additionally, properties with pools in Summerland Key cost, on average, $561 a night. Most of the available vacation rentals with pools are hotel room. You can also rent an accommodation providing a pool near the water, which is the case for nearly half of the rentals there.

Information about vacation rentals in Summerland Key

🏡 Vacation rentals available 197 rentals
🌙 Nightly prices starting at $156
⭐ Popular amenities Pool, Pets allowed and Air conditioning
🐾 Pet friendly homes 96 homes
🏊 Vacation rentals with pools 124 homes

Frequently Asked Questions

What is the typical nightly price for a vacation rental in Summerland Key?

On average, vacation rentals in Summerland Key cost around $156 per night. $536 is the average nightly price for house rentals in Summerland Key. Cottages in Summerland Key cost on average $291 per night.

How many vacation rentals are available for booking in Summerland Key?

Currently there are 197 rentals in Summerland Key to browse and rent for your next trip.

How many vacation rentals with a pool are in Summerland Key?

Summerland Key offers 124 Hotel room and Motel available for booking.

Are pets allowed in vacation rentals in Summerland Key?

Absolutely, currently there are 96 rentals in Summerland Key that allow pets and the average price is $546 per night.

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