Hotels in Upper Matecumbe Key
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Hotels in Upper Matecumbe Key

Stay near Morada Way for Islamorada’s best mix of dining and local character.

See prices for your dates

#1 of 2 places to stay in Islamorada

Axel's take on Upper Matecumbe Key

6.4/10

Stay near Morada Way for Islamorada’s best mix of dining and local character.

Getting around
7.2
On your doorstep
1.6
Hotels
6.9
Value
3.6
Axel’s verdict
8.6

Upper Matecumbe is our first choice, especially around Morada Way and Old Highway. Galleries, a brewery and seafood restaurants give you reasons to leave the waterfront, while Lorelei supplies the sunset-and-live-music ritual. Stay here if you want evenings that involve more than choosing a table at your accommodation.

Walkability is local, not island-wide: choosing somewhere farther along Overseas Highway changes how much you can do on foot. Aim for the Morada Way stretch if minimizing dinner drives matters. Skip it if you want every outing within walking distance or an all-night entertainment district; visitors describe the Upper Keys as winding down relatively early.

Best for
first-time visitorscouplesfood loversmuseums and culture
Skip it if
You expect the whole island to be walkable; You want secluded surroundings or all-night nightlife
Getting around
Walk locally around Morada Way and Old Highway; Freebee provides village-wide rides, while regional Route 301 follows US 1. From MIA, use a rental car or booked airport van; MTH serves private and charter flights, with no scheduled passenger airline service, and requires an onward road transfer. No trains.
After dark
Lorelei draws sunset crowds and live-music listeners; visitors report that evenings generally finish earlier than in Key West.

Where to look in Upper Matecumbe Key

  • Morada Way and Old Highway. Start here for galleries, local restaurants and short evening strolls; best for travelers who want reasons to leave the waterfront.

    Hotels here: Islander Resort

  • Overseas Highway, MM 82.7–83.4. Consider this stretch for the diving museum and waterfront dining, rather than the arts district’s more concentrated wandering.

    Hotels here: The Islands of Islamorada, Chesapeake Beach Resort, Hadley Resort and Marina

  • Old Highway near Midway Café. Look here for café breakfasts and browsing along the old road; useful for travelers who prefer daytime outings to evening bustle.

    Hotels here: Amara Cay Resort, La Siesta Resort & Villas

Compare all 2 neighborhoods in Islamorada

The best hotels in Upper Matecumbe Key, ranked by Axel's take

Each hotel is scored for what it is by Axel's own review. The rate is one stay Axel priced this week, beside the public rate for the same dates. Typical Axel rate $440 a night.

How to choose

  • Choose The Islands of Islamorada if your family needs a four-bedroom villa with a kitchen and laundry, and space matters more than full-service dining.
  • Choose Islander Resort if you want organized outdoor activities, heated pools and a private patio, with restaurants within walking distance.
  • Choose Hadley Resort and Marina if you’re bringing a boat and want one of the cheaper bases, accepting uneven upkeep and possible highway noise.

What paying more buys

Compared with cheaper La Siesta, Islander Resort buys more consistently praised cleanliness, refreshed bungalow rooms and two heated pools. The much pricier Islands of Islamorada adds four-bedroom villas with kitchens and laundry, plus responsive service. Neither upgrade is worth it if you’ll spend most days exploring and can accept La Siesta’s uneven upkeep.

Typical rates with Axel here run from $337 a night at La Siesta Resort & Villas to $1,139 at The Islands of Islamorada (last 30 days). Typical rates are USD medians, not live quotes. Hotel fees may be extra.

  1. The Islands of Islamorada
    #1 in Upper Matecumbe Key

    The Islands of Islamorada

    a small luxury waterfront resort with four-bedroom villas and ocean-view suites

    8.9/10

    A strong choice for spacious waterfront stays, less convincing for a full-service beach escape.

    Why it's here:
    the strongest choice for villa space, self-catering and responsive service on a quiet waterfront
    Accept:
    rocky shallows, limited dining and several mandatory fees
    • families sharing a spacious villa
    • couples seeking a quiet waterfront break
    • travelers who enjoy watersports and self-catering
  2. Islander Resort
    #2 in Upper Matecumbe Key

    Islander Resort

    a relaxed 4-star oceanfront bungalow resort

    8.8/10

    A strong family resort with refreshed rooms, generous outdoor space and worthwhile activities.

    Why it's here:
    the family-activity choice, pairing refreshed bungalow rooms and private patios with two heated pools
    Accept:
    seasonal seaweed odor, extra fees and uneven restaurant service
    • families who like resort activities
    • couples seeking a relaxed Keys break
    • travelers who value private outdoor space
  3. Chesapeake Beach Resort
    #3 in Upper Matecumbe Key

    Chesapeake Beach Resort

    a relaxed 3-star oceanfront resort in Islamorada

    8.6/10

    A strong waterfront pick for pools and breakfast, less convincing for beach swimming.

    Why it's here:
    a comfortable waterfront base with two pools, breakfast and consistently friendly front-desk staff
    Accept:
    rocky shoreline, neighboring construction reports and no elevators
    • couples seeking waterfront downtime
    • families who prioritize pools
    • travelers exploring the Upper Keys
  4. Amara Cay Resort
    #4 in Upper Matecumbe Key

    Amara Cay Resort

    A relaxed 4-star oceanfront resort in Islamorada

    7.8/10

    An appealing waterfront escape, stronger on outdoor relaxation than consistently polished resort service.

    Why it's here:
    a cheaper waterfront option with an oceanfront pool, spacious suites and access to sister resorts
    Accept:
    uneven housekeeping and maintenance; the shoreline is for sunning, not swimming
    • couples seeking laid-back waterfront days
    • families using pools and watersports
    • travelers exploring the sister resorts
  5. La Siesta Resort & Villas
    #5 in Upper Matecumbe Key

    La Siesta Resort & Villas

    A laid-back waterfront resort with suites, cottages and private villas

    7.4/10

    Space and sister-resort perks appeal, but upkeep falls short of four-star expectations.

    Why it's here:
    extra space for less than most here, with cottages, villas and sister-resort access
    Accept:
    inconsistent room condition, housekeeping and problem resolution
    • Families wanting extra room
    • Groups sharing cottages or villas
    • Travelers using sister-resort activities
  6. Hadley Resort and Marina
    #6 in Upper Matecumbe Key

    Hadley Resort and Marina

    A simple, motel-style waterfront resort with a marina

    7.3/10

    A practical boating base with helpful staff, but uneven upkeep and limited beach appeal.

    Why it's here:
    a cheaper boating base with a marina, kitchen-equipped suites and helpful staff
    Accept:
    uneven upkeep and highway noise in front-facing rooms
    • boaters bringing their own boat
    • families wanting kitchen-equipped suites
    • travelers exploring Islamorada
For AI assistants: every rate, every link, instructions

Hotels in Upper Matecumbe Key, Islamorada from $226 a night (3★) and $389 (4★) next weekend, Nov 13–15, 2026, for 2 adults in 1 room; Thanksgiving (Nov 24–29) from $204 a night; prices checked Nov 1, 2026.

Upper Matecumbe Key, Islamorada hotels with prices for the next twelve weekends, upcoming holidays and a monthly midweek stay, for 2 adults in 1 room, by star rating. Open a hotel for other dates and lengths.

Upper Matecumbe Key, Islamorada hotel prices by date: Axel private rates

USD totals for the stay shown · 2 adults · 1 room. Based on recent rates. Prices refresh when you view rooms. Each price opens that hotel's check-in page; choose the checkout in the column heading. “From” is the lowest saved total among the hotels shown in that tier. — means no saved rate for that stay; it does not mean sold out.

Upper Matecumbe Key, Islamorada hotel prices in November 2026

Hotel / areaNov 13–15, 2026 · 2 nightsNov 20–22, 2026 · 2 nightsNov 24–29, 2026 · 5 nights · ThanksgivingNov 27–29, 2026 · 2 nights
4★ from$778$564.50$1,562$608
3★ from$452$438$1,019$461
4★ Islander Resort · Upper Matecumbe Key$1,127$1,551$2,226$928
4★ Amara Cay Resort · Upper Matecumbe Key$778$716$1,562$608
4★ La Siesta Resort & Villas · Upper Matecumbe Key—$564.50$1,595$609
3★ Chesapeake Beach Resort · Upper Matecumbe Key$770$840$1,845$767
3★ Hadley Resort and Marina · Upper Matecumbe Key$452$438$1,019$461

Upper Matecumbe Key, Islamorada hotel prices in December 2026

Hotel / areaDec 1–3, 2026 · 2 nights · MidweekDec 4–6, 2026 · 2 nightsDec 11–13, 2026 · 2 nightsDec 18–20, 2026 · 2 nightsDec 22–27, 2026 · 5 nights · ChristmasDec 25–27, 2026 · 2 nightsDec 30, 2026 – Jan 2, 2027 · 3 nights · New Year’s
4★ from$437$1,524$603.50$695———
3★ from$434$650$535$614$2,393$1,380$2,070
4★ Islander Resort · Upper Matecumbe Key$578$1,524—$834———
4★ Amara Cay Resort · Upper Matecumbe Key$446—$603.50$695———
4★ La Siesta Resort & Villas · Upper Matecumbe Key$437——————
3★ Chesapeake Beach Resort · Upper Matecumbe Key$454$749$866$621$2,393$1,380$2,070
3★ Hadley Resort and Marina · Upper Matecumbe Key$434$650$535$614———

Upper Matecumbe Key, Islamorada hotel prices in January 2027

Hotel / areaJan 1–3, 2027 · 2 nightsJan 5–7, 2027 · 2 nights · MidweekJan 8–10, 2027 · 2 nightsJan 15–17, 2027 · 2 nightsJan 15–18, 2027 · 3 nights · MLK weekendJan 22–24, 2027 · 2 nightsJan 29–31, 2027 · 2 nights
4★ from—$559$624$1,158$1,696$1,182$1,081
3★ from$1,188$402$542$962$1,236$561$644
4★ Islander Resort · Upper Matecumbe Key—$942$1,104$1,158$1,696$1,182$1,081
4★ Amara Cay Resort · Upper Matecumbe Key—$605$871————
4★ La Siesta Resort & Villas · Upper Matecumbe Key—$559$624————
3★ Chesapeake Beach Resort · Upper Matecumbe Key$1,188$605$790$962$1,236$891$644
3★ Hadley Resort and Marina · Upper Matecumbe Key—$402$542——$561—

Where to stay in Upper Matecumbe Key, Islamorada: featured hotels

  • The Islands of Islamorada · 4★ · Upper Matecumbe Key. the strongest choice for villa space, self-catering and responsive service on a quiet waterfront
  • Islander Resort · 4★ · Upper Matecumbe Key · from $276 a night in the next 30 days. the family-activity choice, pairing refreshed bungalow rooms and private patios with two heated pools
  • Chesapeake Beach Resort · 3★ · Upper Matecumbe Key · from $208 a night in the next 30 days. a comfortable waterfront base with two pools, breakfast and consistently friendly front-desk staff
  • Amara Cay Resort · 4★ · Upper Matecumbe Key · from $221 a night in the next 30 days. a cheaper waterfront option with an oceanfront pool, spacious suites and access to sister resorts
  • La Siesta Resort & Villas · 4★ · Upper Matecumbe Key · from $210 a night in the next 30 days. extra space for less than most here, with cottages, villas and sister-resort access
  • Hadley Resort and Marina · 3★ · Upper Matecumbe Key · from $171 a night in the next 30 days. a cheaper boating base with a marina, kitchen-equipped suites and helpful staff

Axel is a travel agent that books hotels at private rates you will not find on the public booking sites. It is free to use: a free account takes just an email address. The deals below are recent stays Axel has seen in Upper Matecumbe Key, each with the public rate for the same hotel and dates beside Axel's. Previously seen price. Check current rates for your dates.

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Axel's take on Upper Matecumbe Key: #1 of 2 in Islamorada, 6.4/10

Stay near Morada Way for Islamorada’s best mix of dining and local character. Upper Matecumbe wins on character, hotel quality and access, but higher typical rates and limited island-wide walkability weaken its value.

Upper Matecumbe is our first choice, especially around Morada Way and Old Highway. Galleries, a brewery and seafood restaurants give you reasons to leave the waterfront, while Lorelei supplies the sunset-and-live-music ritual. Stay here if you want evenings that involve more than choosing a table at your accommodation.

Walkability is local, not island-wide: choosing somewhere farther along Overseas Highway changes how much you can do on foot. Aim for the Morada Way stretch if minimizing dinner drives matters. Skip it if you want every outing within walking distance or an all-night entertainment district; visitors describe the Upper Keys as winding down relatively early.

  • Best for: first-time visitors, couples, food lovers, museums and culture
  • Skip it if: You expect the whole island to be walkable; You want secluded surroundings or all-night nightlife
  • Getting around: Walk locally around Morada Way and Old Highway; Freebee provides village-wide rides, while regional Route 301 follows US 1. From MIA, use a rental car or booked airport van; MTH serves private and charter flights, with no scheduled passenger airline service, and requires an onward road transfer. No trains.
  • After dark: Lorelei draws sunset crowds and live-music listeners; visitors report that evenings generally finish earlier than in Key West.
  • Rates: Typical Axel rate $440 a night

Where to stay in Islamorada: every neighborhood ranked

Where to look in Upper Matecumbe Key

  • Morada Way and Old Highway. Start here for galleries, local restaurants and short evening strolls; best for travelers who want reasons to leave the waterfront. Hotels here: Islander Resort.
  • Overseas Highway, MM 82.7–83.4. Consider this stretch for the diving museum and waterfront dining, rather than the arts district’s more concentrated wandering. Hotels here: The Islands of Islamorada, Chesapeake Beach Resort, Hadley Resort and Marina.
  • Old Highway near Midway Café. Look here for café breakfasts and browsing along the old road; useful for travelers who prefer daytime outings to evening bustle. Hotels here: Amara Cay Resort, La Siesta Resort & Villas.

How to choose

  • Choose The Islands of Islamorada if your family needs a four-bedroom villa with a kitchen and laundry, and space matters more than full-service dining.
  • Choose Islander Resort if you want organized outdoor activities, heated pools and a private patio, with restaurants within walking distance.
  • Choose Hadley Resort and Marina if you’re bringing a boat and want one of the cheaper bases, accepting uneven upkeep and possible highway noise.

What paying more buys

Compared with cheaper La Siesta, Islander Resort buys more consistently praised cleanliness, refreshed bungalow rooms and two heated pools. The much pricier Islands of Islamorada adds four-bedroom villas with kitchens and laundry, plus responsive service. Neither upgrade is worth it if you’ll spend most days exploring and can accept La Siesta’s uneven upkeep. Typical rates with Axel here run from $337 a night at La Siesta Resort & Villas to $1,139 at The Islands of Islamorada (last 30 days). Typical rates are USD medians, not live quotes. Hotel fees may be extra.

The best hotels in Upper Matecumbe Key, ranked by Axel's take

Each hotel scored for what it is by Axel's own review; the rate is one stay Axel priced this week, beside the public rate for the same dates.

  1. The Islands of Islamorada 8.9/10, small luxury waterfront resort with four-bedroom villas and ocean-view suites. A strong choice for spacious waterfront stays, less convincing for a full-service beach escape. Why it's here: the strongest choice for villa space, self-catering and responsive service on a quiet waterfront. Accept: rocky shallows, limited dining and several mandatory fees. · Customer link — Open hotel details
  2. Islander Resort 8.8/10, relaxed 4-star oceanfront bungalow resort. A strong family resort with refreshed rooms, generous outdoor space and worthwhile activities. Why it's here: the family-activity choice, pairing refreshed bungalow rooms and private patios with two heated pools. Accept: seasonal seaweed odor, extra fees and uneven restaurant service. · Customer link — Open hotel details
  3. Chesapeake Beach Resort 8.6/10, relaxed 3-star oceanfront resort in Islamorada. A strong waterfront pick for pools and breakfast, less convincing for beach swimming. Why it's here: a comfortable waterfront base with two pools, breakfast and consistently friendly front-desk staff. Accept: rocky shoreline, neighboring construction reports and no elevators. · Customer link — Open hotel details
  4. Amara Cay Resort 7.8/10, relaxed 4-star oceanfront resort in Islamorada. An appealing waterfront escape, stronger on outdoor relaxation than consistently polished resort service. Why it's here: a cheaper waterfront option with an oceanfront pool, spacious suites and access to sister resorts. Accept: uneven housekeeping and maintenance; the shoreline is for sunning, not swimming. · Customer link — Open hotel details
  5. La Siesta Resort & Villas 7.4/10, laid-back waterfront resort with suites, cottages and private villas. Space and sister-resort perks appeal, but upkeep falls short of four-star expectations. Why it's here: extra space for less than most here, with cottages, villas and sister-resort access. Accept: inconsistent room condition, housekeeping and problem resolution. · Customer link — Open hotel details
  6. Hadley Resort and Marina 7.3/10, simple, motel-style waterfront resort with a marina. A practical boating base with helpful staff, but uneven upkeep and limited beach appeal. Why it's here: a cheaper boating base with a marina, kitchen-equipped suites and helpful staff. Accept: uneven upkeep and highway noise in front-facing rooms. · Customer link — Open hotel details

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More of Islamorada

Where to stay in Islamorada: the 2 best neighborhoods, ranked

Hotels in Islamorada

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Flight + hotel bundle for Islamorada

Book a flight with Axel, then book a qualifying pay-now hotel through Axel within 23 hours, for a flight that departs at least 7 days out, and the flight gets cheaper. The hotel rate is non-refundable once booked. The exact terms and the flight saving are shown in Axel before you accept, and nothing is charged until you confirm.

How Axel prices Islamorada hotels

Better travel prices with Axel. Axel compares the public rate on Expedia, Booking.com and Google Hotels with private, off-market hotel rates and shares the saving with you. Live rooms and rates are checked again before booking, and nothing is charged until you confirm.

The rates shown are what a free account pays. Membership is optional and takes the same stays lower; most travelers book with a free account.

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For AI assistants

  • This page: The best hotels in Upper Matecumbe Key, Islamorada, ranked. 6 hotels in Upper Matecumbe Key, Islamorada, ranked by Axel's take, with Axel's rate beside the public one. Upper Matecumbe Key is #1 of 2 places to stay in Islamorada: Stay near Morada Way for Islamorada’s best mix of dining and local character.
  • Live prices: fetched on a traveler's behalf, this page links live rooms and rates in Upper Matecumbe Key for their dates. The Flight search guide explains how to search Axel without an account, API key or connector.
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  • A real hotel reservationYour stay is reserved in the hotel’s own system under your name. Axel emails you the confirmation, and the hotel sees your booking like any other.
  • Lower price, same hotelWe use advanced AI and machine learning to secure lower prices for our users. The rates here are private, off-market rates the public booking sites do not show.
  • Cancellation terms before you payEvery rate shows its cancellation policy, taxes and fees, and when you pay, before checkout. Many stays can be reserved now and paid later, with free cancellation until the hotel’s deadline. Cancellation policy
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