Find Extended Stay Hotels in Summerland Key, FL

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Top Summerland Key Extended Stay Hotels | Reserve now, pay later

Our top choices for Summerland Key hotels with a kitchen

Exterior
Parmer's Resort

Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1000)
"Room was clean and comfortable."
United States
Barbara K
$178 nightly
The price is $200
Dec 14 - Dec 15
Total with taxes and fees
Parmer's Resort
A heated pool
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.2 out of 10, Very Good, (49)
"Great area. Quiet and comfortable "
United States
nancy c.
$286 nightly
The price is $317
Dec 14 - Dec 15
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
$391 nightly
The price is $434
Dec 14 - Dec 15
Total with taxes and fees
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
House | 2 bedrooms, Internet
Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
$574 nightly
The price is $646
Dec 15 - Dec 16
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views
Fridge, microwave, oven, stovetop
Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (121)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
$463 nightly
The price is $513
Dec 14 - Dec 15
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
Deluxe Villa, Ocean View | 4 bedrooms, laptop workspace, iron/ironing board, free WiFi
Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
$817 nightly
The price is $920
Dec 13 - Dec 14
Total with taxes and fees
Atlantic View Luxury Villa with Pool
Exterior
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
$504 nightly
The price is $560
Dec 14 - Dec 15
Total with taxes and fees
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
A heated pool
Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
2.5 star property
Cudjoe Key
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
$585 nightly
The price is $650
Dec 15 - Dec 16
Total with taxes and fees
Island Time #110 Ocean Views - Cudjoe Key
Outdoor pool, a heated pool
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
7.6 out of 10, Good, (13)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
$432 nightly
The price is $480
Jan 6 - Jan 7, 2026
Total with taxes and fees
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A heated pool
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
$533 nightly
The price is $592
Dec 14 - Dec 15
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Most booked related extended stays in Summerland Key in 2026

Summerland Key apart-hotels
Apart-hotels for extended stays
Apart-hotels for extended stays
Summerland Key vacation homes with a kitchen
Vacation homes with a kitchen
Vacation homes with a kitchen

Frequently asked questions

What are the best long-term hotels in Summerland Key?
Along with kitchens, the best long-term hotels come with plenty of amenities that'll have you feeling at home. Summerland Breeze - A Resort Style Three House Retreat offers conveniences that make a break of a few weeks or longer comfortable, such as a swimming pool and a washing machine. Pool Home On Tranquil Private Cruikshank Island is another in-demand pick. A washing machine and shopping help make this place a standout choice if you're thinking about an extended stay in Summerland Key.
What are the top pet-friendly extended stay hotels in Summerland Key?
Book a pet-friendly room for you and your best chum at Summerland Breeze - A Resort Style Three House Retreat. Spend your extended stay in Summerland Key here and make the most of pet-friendly services and free WiFi. Pet owners are also well taken care of at Deep/wide/flow - Though Canal, 1st Canal From Open Water. This property has a garden, pet-friendly services and other useful amenities that'll help make you and Fido feel at home and relaxed.
What's the best extended stay hotel in downtown Summerland Key?
Book Summerland Breeze - A Resort Style Three House Retreat and get more out of your visit to Summerland Key. This extended stay hotel has a barbecue grill and a dining table and makes the ideal base for exploring. Pool Home On Tranquil Private Cruikshank Island also puts you amid the action. A washing machine and a nearby laundromat are among the amenities that help make this getaway popular with long-term visitors.
What are the best extended stay hotels with kitchens in Summerland Key?
Go sightseeing and then head back and whip up a tasty homestyle meal at 3 Bedroom Accommodation In Summerland Key. Featuring a kitchen, a king bed and a barbecue grill, it has amenities that are made for a long-term stay with the family. Forever Summer is another top property with a kitchen. Take advantage of a swimming pool, a king bed and more during your visit to Summerland Key.
Can I find extended stay hotels with pools in Summerland Key?
For a vacation with plenty of poolside relaxation, choose Waterfront, Two - Story House W. Good times by the pool will be your priority at this popular retreat, which also features a washing machine and a sofa bed. Another excellent choice is 3 Bedroom Accommodation In Summerland Key. Spend your days splashing about in the water and take advantage of the conveniences here, including an oven and a barbecue grill. Rather cook your own meals instead of eating out? Both hotels are equipped with a kitchen, making them perfect for an extended stay in Summerland Key.Summerland Key has a tropical savanna climate and temperatures range between 82 ºF and 84 ºF in the summer months. If you'd love to spend a large portion of your escape swimming, this is an ideal time to visit.
Why book an extended stay hotel in Summerland Key through Expedia?
From our competitive rates to our rewards and members programs, you'll always save when you reserve your extended stay in Summerland Key through Expedia. Add in your travel dates to see our long-term rentals, then fine-tune your search using the filters to find your ideal pad. Our extended stay hotels in Summerland Key come packed with conveniences like kitchens, dining areas and recreational facilities to help make your long-term stay nice and comfy. Whether you're on the hunt for a hotel for a couple of days or somewhere with unbeatable weekly rates, Expedia will help you find a place that's right for you.
What can I expect from an extended stay hotel?
Lock in an extended stay hotel in Summerland Key and take all the time you need experiencing this popular destination. Besides being able to stay a couple of weeks or longer, these types of properties include conveniences that'll make your journey an easy one. Kitchens, dining and laundry areas are just the start. To find your dream extended stay hotel, use Expedia's filters to fine-tune your search based on amenities, price, location and more. Often offering competitive weekly rates, extended stay hotels can be more affordable than a standard hotel option.

Top Summerland Key Hotel Reviews

Parmer's Resort

Parmer's Resort

10/10 Excellent
"The room was OK! Only problem was the TV. It is hanging on the wall next to the front door so that you can hit your head. The room was clean and staff great! "
Barbara 4-night trip
Posted 6 days ago
Parmer's Resort

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